2021/10/21 更新

写真a

ニシハラ ヤスシ
西原 康師
NISHIHARA Yasushi
所属
異分野基礎科学研究所 教授
職名
教授
プロフィール
[最終学歴] 総合研究大学院大学 数物科学研究科 博士後期課程 中退 (1996年)
[学位]博士(理学) 総合研究大学院大学 (1997年) (指導教員:高橋 保 先生)
[担当授業科目](学部)
前期:有機化学 1-2,化学実験 1(分担),自然科学入門(分担)
後期:有機化学 7-8, 化学実験 2(分担),化学ゼミナールB(分担)
(大学院前期課程) 後期:有機金属触媒化学
(大学院後期課程) 前期:合成有機分子化学,動態機能化学演習
[専門分野]有機合成化学,有機金属化学,高分子化学,有機材料化学
[キーワード]遷移金属触媒,有機薄膜太陽電池,有機電界効果トランジスタ,結合の活性化,有機ホウ素化学,有機ケイ素化学,有機フッ素化学
[所属学会] 日本化学会,有機合成化学協会,高分子学会,錯体化学会,近畿化学協会,ケイ素化学協会,アメリカ化学会,応用物理学会
[研究内容] 有機金属錯体触媒を利用した新規有機合成反応の開発と機能性材料への応用
[研究の目標] これまでにない活性や選択性を発現するような新規な有機金属錯体触媒を設計,合成し,新規かつ高選択的な有機合成反応を開発することを研究目的にしています。
その研究過程で多くの海外,国内の研究者との交流を深めながら研究生活(人生)を楽しみたいと考えています。
外部リンク

学位

  • 学士(理学) ( 広島大学 )

  • 修士(理学) ( 広島大学 )

  • 博士(理学) ( 総合研究大学院大学 )

研究キーワード

  • 有機金属化学

  • transistors

  • organic photovoltaics

  • 機能性材料

  • functional materials

  • organometallic chemistry

  • トランジスタ

  • 有機太陽電池

研究分野

  • ナノテク・材料 / 高分子化学

  • ナノテク・材料 / 有機合成化学

  • ライフサイエンス / 生物有機化学

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ナノテク・材料 / 機能物性化学

学歴

  • 総合研究大学院大学   Graduate School, Division of Mathematical and Physical Science  

    - 1996年

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  • 総合研究大学院大学    

    - 1996年

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    国名: 日本国

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  • 広島大学   Graduate School, Division of Natural Science   Department of Chemistry

    - 1994年

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  • 広島大学    

    - 1994年

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    国名: 日本国

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  • 広島大学   理学部   化学科

    - 1992年

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    国名: 日本国

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  • 広島大学   Faculty of Science   Department of Chemistry

    - 1992年

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経歴

  • - 岡山大学異分野基礎科学研究所 教授

    2016年

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  • - Professor,Research Institute for Interdisciplinary Science

    2016年

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  • Professor,Graduate School of Natural Science and Technology

    2010年 - 2016年

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  • 岡山大学大学院自然科学研究科 教授   The Graduate School of Natural Science and Technology

    2010年 - 2016年

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  • - Professor,Graduate School of Natural Science and Technology,Okayama University

    2010年

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  • - 岡山大学自然科学研究科 教授

    2010年

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  • Associate Professor,Chemistry and Biochemistry,Graduate School of Natural Science and Technology,Okayama University

    2007年 - 2010年

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  • 岡山大学大学院自然科学研究科 准教授   The Graduate School of Natural Science and Technology

    2007年 - 2010年

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  • 岡山大学自然科学研究科機能分子化学専攻 准教授

    2007年 - 2010年

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  • Associate Professor

    2007年 - 2010年

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  • Associate Professor,Chemistry and Biochemistry,Graduate School of Natural Science and Technology,Okayama University

    2005年 - 2007年

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  • 岡山大学大学院自然科学研究科 助教授   The Graduate School of Natural Science and Technology

    2005年 - 2007年

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  • 岡山大学自然科学研究科機能分子化学専攻 助教授

    2005年 - 2007年

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  • Associate Professor,Associate Professor of The Graduate School of Natural Science and Technology Okayama University

    2005年 - 2007年

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  • 岡山大学 理学部化学科 助教授   Faculty of Science

    2004年 - 2005年

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  • 岡山大学理学部化学科 助教授   Faculty of Science

    2004年 - 2005年

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  • Associate Professor,Associate Professor of Chemistry Department, Okayama University

    2004年 - 2005年

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  • Associate Professor,Dept. of Chemistry,Faculty of Science,Okayama University

    2004年 - 2005年

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  • Research Associate,Assistant Professor of Chemistry Resources Laboratory, Tokyo Institute of Technology

    1996年 - 2004年

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  • 東京工業大学 資源化学研究所 助手   Chemical Resources Laboratory

    1996年 - 2004年

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  • 日本学術振興会 特別研究員 日本学術振興会特別研究員

    1996年

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  • Postdoctoral Fellowships of Japan Society for the Promotion of Science,JSPS Research Fellow(The Graduate University for Advanced Studies)

    1996年

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所属学協会

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委員歴

  • 高分子学会   中国四国支部 理事  

    2010年   

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    団体区分:学協会

    高分子学会

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  • 日本化学会   座長  

    2009年   

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    団体区分:学協会

    日本化学会

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  • The First International Symposium of Chemistry and Biochemistry in East Asia   プログラム委員長/オーガナイザー/座長  

    2009年   

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    団体区分:学協会

    The First International Symposium of Chemistry and Biochemistry in East Asia

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  • The First International Symposium of Chemistry and Biochemistry in East Asia   プログラム委員長/オーガナイザー/座長  

    2008年   

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    団体区分:学協会

    The First International Symposium of Chemistry and Biochemistry in East Asia

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論文

  • Nickel/copper-cocatalyzed decarbonylative silylation of acyl fluorides 査読

    Wang Xiu, Wang Zhenhua, Nishihara Yasushi

    CHEMICAL COMMUNICATIONS   55 ( 71 )   10507 - 10510   2019年9月

  • Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides 査読

    Wang Zhenhua, Wang Xiu, Ura Yasuyuki, Nishihara Yasushi

    ORGANIC LETTERS   21 ( 17 )   6779 - 6784   2019年9月

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    掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/acs.orglett.9b02398

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  • Transistor Properties of Semiconducting Polymers Based on Vinylene-bridged Difluorobenzo[c][1,2,5]thiadiazole (FBTzE) 査読

    Asanuma Yuya, Mori Hiroki, Nishihara Yasushi

    CHEMISTRY LETTERS   48 ( 9 )   1029 - 1031   2019年9月

  • PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp(3))-O Bond Cleavage Accelerated by TBAT 査読

    Wang Zhenhua, Wang Xiu, Nishihara Yasushi

    CATALYSTS   9 ( 7 )   2019年7月

  • Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe3 査読

    Wang Xiu, Wang Zhenhua, Asanuma Yuya, Nishihara Yasushi

    ORGANIC LETTERS   21 ( 10 )   3640 - 3643   2019年5月

  • Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions 査読

    Wang Xiu, Wang Zhenhua, Liu Li, Asanuma Yuya, Nishihara Yasushi

    MOLECULES   24 ( 9 )   2019年5月

  • Copper-catalyzed Regioselective Chloroamination of Alkenes with Chlorotrimethylsilane and N-Fluorobenzenesulfonimide under Microwave-assisted Conditions 査読

    Iwasaki Masayuki, Xu Jie, Tani Yukari, Fu Liyan, Ikemoto Yuichi, Ura Yasuyuki, Nishihara Yasushi

    CHEMISTRY LETTERS   48 ( 3 )   281 - 284   2019年3月

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    掲載種別:研究論文(学術雑誌)  

    DOI: 10.1246/cl.180937

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  • Vinylene-bridged difluorobenzo[c][1,2,5]-thiadiazole (FBTzE): a new electron-deficient building block for high-performance semiconducting polymers in organic electronics 査読

    Asanuma Yuya, Mori Hiroki, Takahashi Ryosuke, Nishihara Yasushi

    JOURNAL OF MATERIALS CHEMISTRY C   7 ( 4 )   905 - 916   2019年1月

  • Synthesis and Physicochemical Properties of Dibenzo[2,3-d:2 ',3 '-d ']anthra[1,2-b:5,6-b ']dithiophene (DBADT) and Its Derivatives: Effect of Substituents on Their Molecular Orientation and Transistor Properties 査読

    Hyodo Keita, Nishinaga Shuhei, Sawanaka Yuta, Ishida Takumi, Mori Hiroki, Nishihara Yasushi

    JOURNAL OF ORGANIC CHEMISTRY   84 ( 2 )   698 - 709   2019年1月

  • Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene Derivatives: Synthesis and effect of sulfur positions on their transistor properties 査読

    Shuhei Nishinaga, Masato Mitani, Hiroki Mori, Toshihiro Okamoto, Jun Takeya, Yasushi Nishihara

    Bulletin of the Chemical Society of Japan   92 ( 6 )   1107 - 1116   2019年

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    掲載種別:研究論文(学術雑誌)  

    © 2019 The Chemical Society of Japan. Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene (BBTBDT-2) and its phenyl-substituted derivative were successfully synthesized and characterized. From DFT calculations, highest occupied molecular orbitals (HOMOs) of both compounds are well delocalized and large orbital coefficients exist on sulfur atoms. Single-crystal X-ray analysis revealed that BBTBDT-2 derivatives formed herringbone structures in the solid state. In particular, BBTBDT-2 formed a layer-by-layer structure with effective 2D charge-carrier transporting capability. The fabricated OFETs based on BBTBDT-2 gave mobility up to 0.49 cm2 V11 s11 in the vacuum-deposited thin films, which is the highest value among BBTBDT derivatives including our previously reported syn-counterparts. We have also clarified a detailed structureproperty relationship of sulfur positions and phenyl substituents as indicated by theoretical calculation, GIWAXS, and AFM analyses.

    DOI: 10.1246/bcsj.20180358

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  • Development of a phenanthrodithiophene-difluorobenzoxadiazole copolymer exhibiting high open-circuit voltage in organic solar cells 査読

    Mori Hiroki, Takahashi Ryosuke, Nishihara Yasushi

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   56 ( 23 )   2646 - 2655   2018年12月

  • Nickel-catalysed decarbonylative borylation of aroyl fluorides 査読

    Zhenhua Wang, a, Xiu Wanga, Yasushi Nishihara

    Chem. Commun.   2018年11月

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  • Synthesis and Transistor Characteristics of Dinaphtho[2,3-d:2 ',3 '-d ']anthra[1,2-b:5,6-b ']dithiophene (DNADT) 査読

    Nishinaga Shuhei, Sawanaka Yuta, Toyama Ryota, Ishida Takumi, Mori Hiroki, Nishihara Yasushi

    CHEMISTRY LETTERS   47 ( 11 )   1409 - 1411   2018年11月

  • Development of a Phenanthrodithiophene-Difluorobenzoxadiazole Copolymer Exhibiting High Open-Circuit Voltage in Organic Solar Cells 査読

    Hiroki Mori, Ryosuke Takahashi, Yasushi Nishihara

    J. Poly. Sci. Part A: Pol. Chem.   56   2646 - 2655   2018年10月

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  • Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Fluorides Assisted by Lewis-Acidic Organoboranes 査読

    Yasuhiro Okuda, Jie Xu, Takumi Ishida, Chen-an Wang, Yasushi Nishihara

    ACS Omega   3   13129 - 13140   2018年10月

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  • Synthesis and Transistor Characteristics of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) 査読

    Shuhei Nishinaga, Yuta Sawanaka, Ryota Toyama, Takumi Ishida, Hiroki Mori, Yasushi Nishihara

    Chem. Lett.   47   1409 - 1411   2018年9月

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    記述言語:英語  

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  • Regioselective Synthesis of γ‑Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α‑Halocarboxylic Acids and Their Derivatives 査読

    Masayuki Iwasaki, Natsumi Miki, Yuichi Ikemoto, Yasuyuki Ura, Yasushi Nishihara

    Org. Lett.   20   3848 - 3852   2018年6月

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    記述言語:英語  

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  • Alkoxy-Substituted Anthra[1,2-c:5,6-c’]bis([1,2,5]-thiadiazole) (ATz): a New Electron-Acceptor Unit in the Semiconducting Polymers for Organic Electronics 査読

    Hiroki Mori, Shuhei Nishinaga, Ryosuke Takahashi, Yasushi Nishihara

    Macromolecules   51   5473 - 5484   2018年6月

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    記述言語:英語  

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  • Low-bandgap semiconducting polymers based on sulfur-containing phenacene-type molecules for transistor and solar cell applications 査読

    Hiroki Mori, Yasushi Nishihara

    Polymer Journal   50   1 - 11   2018年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Nature Publishing Group  

    The incorporation of a highly extended π-electron system into a polymer backbone is an effective strategy to develop high-performance donor–acceptor (D–A) polymers suitable for organic electronics because this strategy can facilitate a dense π-π stacking structure, leading to efficient carrier transport. With this in mind, we developed phenanthro[1,2-b:8,7-b′]dithiophene (PDT) because this new phenacene-type molecule has a highly crystalline nature, deep HOMO level, and high hole mobility, which are characteristics known to be suitable for a donor unit in high-performance D–A polymers. In this focus review, we report recent progress in PDT-containing D-A polymers combined with various strong acceptor units. Incorporation of PDT into a polymer backbone results in deep HOMO energy levels of −5.4~−5.5 eV, strong aggregation, and a dense packing structure with a short π-stacking distance of 3.5~3.6 Å. PDT-based polymers with appropriate alkyl side chains exhibit high hole mobilities of up to 0.18 cm2 V−1 s−1 in organic field-effect transistor (OFET) devices due to their tendency to form highly ordered edge-on structures. Furthermore, we can adjust their level of molecular orientation from edge-on to face-on by increasing their molecular weight, leading to a high power conversion efficiency of over 6% in polymer solar cell (PSC) applications. These results demonstrate that PDT is a good candidate as a high-performance building block in D-A polymers.

    DOI: 10.1038/s41428-018-0072-4

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  • Efficient Synthesis and Properties of [1]Benzothieno[3,2-b]thieno[2,3-d]furans and [1]Benzothieno[3,2-b]thieno[2,3-d]thiophenes 査読

    Yuji Kurimoto, Koichi Mitsudo, Hiroki Mandai, Atsushi Wakamiya, Yasujiro Murata, Hiroki Mori, Yasushi Nishihara, Seiji Suga

    Asian J. Org. Chem.   7   1635 - 1641   2018年5月

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  • Effect of Substitution Positions of Alkyl Side Chains in Phenanthrodithiophene–Isoindigo Copolymers: The Enhancement of Crystallinity and Control of Molecular Orders 査読

    Hiroki Mori, Shuto Hara, Ryota Toyama, Yuya Asanuma, Ryosuke Takahashi, Shuhei Nishinaga, Yasushi Nishihara

    J. Poly. Sci. Part A: Pol. Chem.   56   1757 - 1767   2018年5月

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  • Phenanthrodithiophene (PDT)-Difluorobenzothiadiazole (DFBT) Copolymers: Effect on Molecular Orientation and Solar Cell Performance of Alkyl Substitution onto a PDT Core 査読

    Hiroki Mori, Ryosuke Takahashi, Keita Hyodo, Shuhei Nishinaga, Yuta Sawanaka, Yasushi Nishihara

    Macromolecules   51 ( 4 )   1357 - 1369   2018年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Synthesis, characterization, and solar cell application of three 4,7-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT)-difluorobenzothiadiazole (DFBT copolymers (P1-P3) with different linear alkyl side chains to improve solubility, molecular weight, and molecular orientation are described. The utilization of Ir-catalyzed direct borylation and sequential functionalization can selectively afford the target 4,7-dialkylated PDT as the monomers. Migita-Kosugi-Stille coupling in the presence of CuI can accelerate polymerization to afford high-molecular-weight polymers along with their improved solubility. The effect of alkyl substitution at the 4,7-positions on the electronic structure of PDT-DFBT copolymers is negligible. By installation of additional alkyl chains at the 4,7-positions of PDT, the synthesized polymers P1-P3 have lower intermolecular interaction than that of nonalkylated P0, but they still maintained aggregation behavior in solution. In addition, they formed a favorable face-on orientation with a short π-stacking distance of 3.6 Å, which can enhance their carrier transport ability, resulting in high Jsc and FF. As a result, their fabricated solar cells reached a PCE exceeding 6%, which are about 1.7-fold higher than that of P0. Comparison of alkyl side chain length at the 4,7-positions of PDT revealed that all polymers formed a predominantly face-on orientation and have a similar face-on ratio in blended films, but their crystallinity was decreased as the carbon chains at the 4,7-positions of PDT became shorter. On the other hand, the polymers with short alkyl side chains tended to have low surface roughness and small domain size of active layers, which is an ideal phase separation structure for high-performance PSCs. From these results, it could be seen that the polymers have a trade-off relationship between their domain size and crystallinity, but the impact of alkyl side chain length on their photovoltaic properties is rather small. Thus, the construction of face-on orientation is highly important to achieve a high PCE. Among three polymers, the P3/PC61BM-based solar cell with an optimal nanoscale phase separation structure with bicontinuous domain showed the highest PCE of up to 6.6%.

    DOI: 10.1021/acs.macromol.7b02734

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  • Direct Thiolation and Selenation of Aryl C─H Bonds Catalyzed by Palladium or Nickel 査読

    Masayuki Iwasaki, Yasushi Nishihara

    J. Syn. Org. Chem. Jpn. (Yuki Gosei Kagaku Kyokaishi)   76 ( 1 )   11 - 20   2018年

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  • Synthesis of a 1,2-Dithienylethene-Containing Donor-Acceptor Polymer via Palladium-Catalyzed Direct Arylation Polymerization (DArP) 査読

    Masayuki Wakioka, Natsumi Yamashita, Hiroki Mori, Yasushi Nishihara, Fumiyuki Ozawa

    Molecules   23 ( 4 )   981 - 990   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:MDPI AG  

    This paper reports the synthesis of D-A polymers containing 1,2-dithienylethene (DTE) units via palladium-catalyzed direct arylation polymerization (DArP). The reaction of dibromoisoindigo (1-Br) and DTE (2-H), in the presence of Pd2(dba)3·CHCl3 (0.5 mol%), P(2-MeOC6H4)3 (L1) (2 mol%), pivalic acid (1 equiv) as catalyst precursors, and Cs2CO3 (3 equiv) as a base affords poly(1-alt-2) with a high molecular weight (Mn up to 44,900). Although, it has been known that monomers, with plural C–H bonds, tend to form insoluble materials via direct arylation at undesirable C–H positions
    the reaction of 1-Br and 2-H cleanly proceeds without insolubilization. The resulting polymer has a well-controlled structure and exhibits good charge transfer characteristics in an organic field-effect transistor (OFET), compared to the polymer produced by Migita–Kosugi–Stille cross-coupling polymerization. The DArP product displays an ideal linear relationship in the current–voltage curve, whereas the Migita–Kosugi–Stille product shows a VG-dependent change in the charge mobility.

    DOI: 10.3390/molecules23040981

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  • Synthesis and Transistor Application of Bis[1]benzothieno[6,7?d:6',7'?d']benzo[1,2-b:4,5-b']dithiophenes 査読

    Shuhei Nishinaga, Hiroki Mori, Yasushi Nishihara

    The Journal of Organic Chemistry   83   5506 - 5515   2018年

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    記述言語:英語  

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  • Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with o-Bromobenzyl Alcohols through Multiple Carbon–Carbon Bond Formations 査読

    Masayuki Iwasaki, Yasuhiro Araki, Yasushi Nishihara

    J. Org. Chem.   82 ( 12 )   6242 - 6258   2017年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/acs.joc.7b00848

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  • Solar Cell Performance of Phenanthrodithiophene-Isoindigo Copolymers Depends on Their Thin-Film Structure and Molecular Weight 査読

    Hiroki Mori, Shuto Hara, Shuhei Nishinaga, Yasushi Nishihara

    MACROMOLECULES   50 ( 12 )   4639 - 4648   2017年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Phenanthro[1,2-b:8,7-b']dithiophene (PDT)isoindigo (IID)-based polymers 12OD (L) and 12OD (H) with a different molecular weight were synthesized and characterized. By using further purified PDT and IID monomers, the high-molecular-weight polymer 12OD (H) with number-average molecular weight (M-n) over 50 kDa was obtained. Both 12OD (L) and 12OD (H) polymers have the same energy gap and highest occupied molecular orbital (HOMO) energy levels, indicating that the influence of molecular weight on their electronic structure is negligible, although 12OD (H) has stronger aggregation behavior than 12OD (L). 12OD (H)-based solar cells fabricated by using optimal solvent and additives showed an increased short-circuit current density (J(sc)) with same open-circuit voltage (V-oc) and fill factor (FF), resulting in a significantly improved power conversion efficiency (PCE) of up to 6.1%, which is approximately 70% higher than that of the 12OD (L)-based cell (3.5%). This result is due to the different molecular orientation caused by the higher molecular weight. Grazing incidence wide-angle X-ray scattering (GIWAXS) analyses revealed that the blended film of 12OD (H)/[6,6]-phenyl-C-61-butyric acid methyl ester (PC61BM) formed a face-on orientation with a long-range ordered structure, while a low crystalline edge-on structure was observed in the blended film of 12OD (L)/PC61BM. Such high crystalline and favorable molecular orientation could promote light harvesting efficiency and hole transporting ability, resulting in high J(sc) and thus an excellent PCE. From the detailed GIWAXS analysis, the orientation change of 12OD (H) was induced by the addition of PC61BM. This result suggests that the strong aggregation ability of 12OD (H) can drive crystallization and favors active interaction with PC61BM to form a face-on orientation. In this study, the increase in molecular weight can improve not only the thin-film structure such as crystallinity and phase separation structure but also the molecular orientation in the PDT-based polymer system.

    DOI: 10.1021/acs.macromol.7b00778

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  • Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp(2))-H Bonds with Elemental Selenium in Air 査読

    Masayuki Iwasaki, Natsumi Miki, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

    ORGANIC LETTERS   19 ( 5 )   1092 - 1095   2017年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.

    DOI: 10.1021/acs.orglett.7b00116

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  • Synthesis and Physicochemical Properties of Piceno[4,3-b:9,10-b′]dithiophene Derivatives and Their Application in Organic Field-Effect Transistors 査読

    Keita Hyodo, Ryota Toyama, Hiroki Mori, Yasushi Nishihara

    ACS Omega   2 ( 1 )   308 - 315   2017年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Efficient synthesis and characterization of several piceno[4,3-b:9,10-b′]dithiophene (PiDT) derivatives by Negishi coupling, epoxidation, and Lewis acid-catalyzed cycloaromatization sequences and their potential utility in organic field-effect transistors (OFETs) have been reported. PiDT derivatives, with extended π-electron systems, showed high air stability due to their deep highest occupied molecular orbital energy levels (around -5.6 eV). OFET devices based on 2,11-dioctylated PiDT (C8-PiDT) showed excellent hole mobility, as high as 2.36 cm2 V-1 s-1. Their structure-property relationships were investigated by X-ray diffraction and atomic force microscopy.

    DOI: 10.1021/acsomega.7b00015

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  • Bis[1]benzothieno[2,3-d:2 ',3 '-d ']anthra[1,2-b:5,6-b ']dithiophene: synthesis, characterization, and application to organic field-effect transistors 査読

    Keita Hyodo, Hideki Hagiwara, Ryota Toyama, Hiroki Mori, Shin-ichi Soga, Yasushi Nishihara

    RSC ADVANCES   7 ( 10 )   6089 - 6092   2017年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    We report the straightforward synthetic method and characterization of bis[1]benzothieno[2,3-d:2',3'-d']anthra[1,2-b:5,6-b']dithiophene (BBTADT) having nine aromatic rings fused without solubilizing groups. The highest mobility of fabricated OFETs utilizing BBTADT exhibited 2.7 x 10(-2) cm(2) V-1 s(-1) in polycrystalline films formed by vapor deposition, depending on the annealing temperatures of a substrate.

    DOI: 10.1039/c6ra27455b

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  • Transistor Properties of 2,7-Dialkyl-Substituted Phenanthro[2,1-b:7,8-b '] dithiophene

    Yoshihiro Kubozono, Keita Hyodo, Shino Hamao, Yuma Shimo, Hiroki Mori, Yasushi Nishihara

    Scientific Reports   6   38535   2016年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:NATURE PUBLISHING GROUP  

    A new phenacene-type molecule with five fused aromatic rings was synthesized: 2,7-didodecylphenanthro[2,1-b: 7,8-b'] dithiophene ((C12H25)(2)-i-PDT), with two terminal thiophene rings. Field-effect transistors (FETs) using thin films of this molecule were fabricated using various gate dielectrics, showing p-channel normally-off FET properties with field-effect mobilities (mu) greater than 1cm(2) V-1 s(-1). The highest mu value in the thin-film FETs fabricated in this study was 5.4 cm(2) V-1 s(-1), when a 150 nm-thick ZrO2 gate dielectric was used. This implies that (C12H25)(2)-i-PDT is very suitable for use in a transistor. Its good FET performance is fully discussed, based on electronic/topological properties and theoretical calculations.

    DOI: 10.1038/srep38535

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  • Highly Selective Synthesis of Multi-substituted Olefins Mediated by Zirconocene Complexes

    Keita Hyodo, Yasushi Nishihara

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   74 ( 8 )   792 - 802   2016年8月

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    記述言語:日本語   出版者・発行元:SOC SYNTHETIC ORGANIC CHEM JPN  

    In this paper, the efficient methodology for the synthesis of multi-substituted olefins by using zirconocene complexes is described. The key step is regioselective formation of zirconacyclopentenes from alkynylboron and alkynylsilane compounds. The subsequent Negishi and Suzuki-Miyaura coupling reactions of C-B and C-Zr bonds give rise to multi-substituted olefins. The developed reaction can be applicable to the synthesis of various functional molecules, for example, an anti-cancer agent. In addition, the mechanism for a regioselective formation of zirconacyclopentenes is analyzed by reactions of alkynylboronates and a zirconocene (II) complex. As a result, it is disclosed that an electrostatic interaction effected the regioselective formation of zirconacyclopentenes. The synthesis of various unprecedented tri- and tetra-alkylated olefins using beta-hydrogen containing alkyl electrophiles and alkylzinc reagents as coupling partners in regio- and stereocontrolled manners is also described.

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  • Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B-Si, B-B, and Cl-S Bonds to Alkynes, and Subsequent Cross-Couplings

    Masayuki Iwasaki, Yasushi Nishihara

    CHEMICAL RECORD   16 ( 4 )   2031 - 2045   2016年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups.

    DOI: 10.1002/tcr.201600017

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  • Palladium-Catalyzed Regio- and Stereoselective Carbothiolation of Terminal Alkynes with Azolyl Sulfides

    Masayuki Iwasaki, Nikola Topolovcan, Hao Hu, Yugo Nishimura, Glwadys Gagnot, Rungsaeng Na Nakorn, Ramida Yuvacharaskul, Kiyohiko Nakajima, Yasushi Nishihara

    ORGANIC LETTERS   18 ( 7 )   1642 - 1645   2016年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Palladium-catalyzed carbothiolation of terminal alkynes with azolyl sulfides affords various 2-(azolyl)alkenyl sulfides with perfect regio- and stereoselectivities. The present addition reaction proceeded through a direct cleavage of carbon-sulfur bonds in azolyl sulfides. The resulting adducts that are useful intermediates in organic synthesis are further transformed to multisubstituted olefins containing azolyl moieties.

    DOI: 10.1021/acs.orglett.6b00503

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  • Highly crystalline, low band-gap semiconducting polymers based on phenanthrodithiophene-benzothiadiazole for solar cells and transistors

    Hiroki Mori, Hikaru Nonobe, Yasushi Nishihara

    POLYMER CHEMISTRY   7 ( 8 )   1549 - 1558   2016年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    New PDT-based polymers were combined with two types of benzothiadiazole (BT) derivatives to improve their crystallinity and solar cell performance. These polymers show several advantages, including strong intermolecular interactions, deep HOMO energy levels, and a dense packing structure with a short pi-pi stacking distance of 3.5-3.6 angstrom. Combinations of PDT and BT units in polymers formed highly crystalline thin films with a long-range order, even in films blended with a fullerene derivative. This suggests that the introduction of optimal acceptor units may increase the regularity of the polymers, leading to effective pi-pi overlaps between the polymer backbones. However, although the present polymers also formed an appropriate phase separation structure in blended films, in fabricated solar cell devices they yielded low power conversion efficiencies (PCEs) not exceeding 3.8%. GI-WAXS analysis revealed that both polymers were present in a predominantly edge-on orientation. This unsuitable orientation for PSCs prevented efficient carrier transport and reduced charge collection efficiency, resulting in low J(sc) and thus low PCE. On the other hand, these polymers also formed highly oriented edge-on structures on n(+)-Si/SiO2 substrates, which are suitable for high-performance field-effect transistors (FETs), and a fabricated FET device showed a hole mobility as high as 0.18 cm(2) V-1 s(-1).

    DOI: 10.1039/c5py01878a

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  • Molecular mechanism of palladium-catalyzed cyanoesterification of methyl cyanoformate onto norbornene 査読

    石塚拓也, 奥田靖浩, Szilagyi, R. K, 森 聖治, 西原康師

    Dalton Trans.   45   7786 - 7793   2016年

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    記述言語:英語  

    DOI: 10.1039/c6dt00341a

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  • Palladium-catalysed direct thiolation and selenation of aryl C-H bonds assisted by directing groups 査読

    Masayuki Iwasaki, Yasushi Nishihara

    DALTON TRANSACTIONS   45 ( 39 )   15278 - 15284   2016年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Direct chalcogenation of aryl C-H bonds has attracted a lot of attention because arylcharcogen compounds represent useful building blocks in bioactive molecules and functional organic materials. Very recently, chelate-assisted intermolecular direct thiolation and selenation have been developed using various transition-metal catalysts such as palladium, rhodium, nickel, copper and ruthenium. In addition, an appropriate choice of directing group can be used to control the reaction sites. This highlight review focuses on the recent advances in catalytic C-H chalcogenation.

    DOI: 10.1039/c6dt02167k

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  • Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C-C Bond Formations Catalyzed by a Palladium Complex

    Masayuki Iwasaki, Yasuhiro Araki, Shohei Iino, Yasushi Nishihara

    J. Org. Chem.   80 ( 18 )   9247 - 9263   2015年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/acs.joc.5b01693

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  • Impact of Alkyl Side Chains on Thin-film Transistor Performances in Phenanthrodithiophene-Isoindigo Copolymers

    Shuhei Nishinaga, Hiroki Mori, Yasushi Nishihara

    CHEMISTRY LETTERS   44 ( 7 )   998 - 1000   2015年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Organic field-effect transistor (OFET) characteristics of phenanthrodithiophene (PDT)-isoindigo (IID) copolymers with different alkyl chains (12OD and BOBO) as an active layer, and their structure property relationships are described. The fabricated 12OD-based OFET device exhibited hole mobility of 0.16 cm(2)V(-1) s(-1). Grazing-incidence wide-angle X-ray scattering (GIWAXS) analysis revealed that 12OD formed highly ordered edge-on structure, whereas the BOBO film showed amorphous-like structure with no obvious pi-stacking crystallites. This may be attributed to a large steric hindrance of branched side chains in the BOBO polymer, which suppresses effective pi-pi overlaps between the adjacent polymer backbones.

    DOI: 10.1246/cl.150357

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  • Phenanthrodithiophene-Isoindigo Copolymers: Effect of Side Chains on Their Molecular Order and Solar Cell Performance

    Shuhei Nishinaga, Hiroki Mori, Yasushi Nishihara

    MACROMOLECULES   48 ( 9 )   2875 - 2885   2015年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The synthesis;,characterization, and solar cell application of newly developed semiconducting polymers containing phenanthro[1,2-b:8,7-b']dithiophene (PDT) combined with A bis(thienyl)isoindigo (IID) unit are,described. The polymers with longer, alkyl Chains are sufficiently soluble to be compatible with the processes required to manufacture solar cells. In conventional solar cell, devices, polymers with all branched alkyl chains tend to form a higher proportion of a well-ordered face-on crystallite in the pi-stack direction than those with both linear and branched alkyl chains, which significantly improves the Ell factor (FF), resulting in higher power conversion efficiency (PCE). In terms of optimizing the alkyl chain lengths; the installation of longer alkyl side chains on the polymer backbone leads to low molecular weight polymer, which may promote a large phase separation. As a result, the polymers 12OD and BOBO, beating shorter alkyl groups, performed better, and a BOBO polymer-based solar cell (PSC) showed the best PCE value up to 3.83%. In the inverted PSCs, the polymers with all branched alkyl chains have a higher face-on ratio than those with both linear and branched alkyl chains. Because of their improved J(sc), inverted PSCs with BOBO/PC71BM gave the best performance, with a PCE up to 5.28%. Although an obvious dependence of photovoltaic properties on molecular order-was observed in conventional solar cell devices, no trend was observed in inverted cells, Possibly attributable to their amorphous nature, which arises from the axisymmetrical structure of PDT, leading to less effective pi-pi overlap and low crystallinity.

    DOI: 10.1021/acs.macromol.5b00622

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  • Erratum: Transistor application of new picene-type molecules, 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophenes (Journal of Materials Chemistry C (2015) 3 DOI: 10.1039/c4tc02413c) 査読

    Yoshihiro Kubozono, Keita Hyodo, Hiroki Mori, Shino Hamao, Hidenori Goto, Yasushi Nishihara

    Journal of Materials Chemistry C   3 ( 12 )   2960   2015年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/c5tc90044a

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  • Synthesis, Characterization, and Solar Cell and Transistor Applications of Phenanthro[1,2-b:8,7-b ']dithiophene-Diketopyrrolopyrrole Semiconducting Polymers

    Hiroki Mori, Masato Suetsugu, Shuhei Nishinaga, Ning-hui Chang, Hikaru Nonobe, Yasuhiro Okuda, Yasushi Nishihara

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   53 ( 5 )   709 - 718   2015年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-BLACKWELL  

    Synthesis, characterization, and polymer solar cell and transistor application of a series of phenanthro[1,2-b:8,7-b]dithiophene-based donor-acceptor (D-A)-type semiconducting polymers combined with a diketopyrrolopyrrole unit are reported. The present polymers showed some unique features such as strong aggregation behavior, high thermal stability, and short - stacking distance (3.5-3.6 angstrom), which are suitable for high performance organic materials. In addition, they have a significantly extended absorption up to 1000 nm with a band gap of ca. 1.2 eV. However, such strong intermolecular interaction reduced their solubility and molecular weights, which resulted in low crystalline nature and moderate field-effect mobility of 0.01 cm(2) V-1 s(-1). Furthermore, such strong aggregation behavior led to the large-scale phase separation in the blend films, which may prevent the effective photocurrent generation, limiting J(sc) and power conversion efficiency of 2.0%. (c) 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 709-718

    DOI: 10.1002/pola.27500

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  • Transistor application of new picene-type molecules, 2,9-dialkylated phenanthro[1,2-b:8,7-b ']dithiophenes

    Yoshihiro Kubozono, Keita Hyodo, Hiroki Mori, Shino Hamao, Hidenori Goto, Yasushi Nishihara

    JOURNAL OF MATERIALS CHEMISTRY C   3 ( 10 )   2413 - 2421   2015年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Field-effect transistors (FETs) have been fabricated with thin films of a series of 2,9-dialkylated phenanthro [1,2-b:8,7-b'] dithiophene derivatives (C-n-PDTs). The FET characteristics of C-n-PDT thin-film FETs with an SiO2 gate dielectric as well as high-k gate dielectrics were recorded, and the dependence of the field-effect mobility, mu, on the number (n) of carbon atoms in the alkyl chains was investigated, showing that the 2,9-didodecylphenanthro[1,2-b:8,7-b'] dithiophene (C-12-PDT) thin-film FET displays superior properties, with mu s as high as 1.8 cm(2) V-1 s(-1) for the SiO2 gate dielectric and 2.2 cm(2) V-1 s(-1) for the HfO2 gate dielectric. The average mu values, <mu >, reach 1.1(5) and 1.8(6) cm(2) V-1 s(-1), respectively, for the SiO2 and ZrO2 gate dielectrics. Low-voltage operation, showing an absolute average threshold voltage <|V-th|> of similar to 11 V, was implemented, together with the above high <mu > of similar to 2 cm(2) V-1 s(-1). Also, a flexible FET was fabricated with a parylene gate dielectric. The results of this study show the potential of the C-12-PDT molecule for application in a high-performance transistor.

    DOI: 10.1039/c4tc02413c

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  • A divergent synthesis of 3,10-dialkylpicenes

    Xi-Chao Chen, Shuhei Nishinaga, Yasuhiro Okuda, Jia-Ji Zhao, Jie Xu, Hiroki Mori, Yasushi Nishihara

    Organic Chemistry Frontiers   2 ( 5 )   536 - 541   2015年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHINESE CHEMICAL SOC  

    A series of 3,10-dialkylated picenes has been synthesized from 3,10-dimethoxypicene through a divergent approach involving Ni-catalyzed alkynylation of a C-O bond, alkylation, and hydrogenation.

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  • Palladium-Catalyzed pen-Selective Chalcogenation of Naphthylamines with Diaryl Disulfides and Diselenides via C-H Bond Cleavage

    Masayuki Iwasaki, Wataru Kaneshika, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

    JOURNAL OF ORGANIC CHEMISTRY   79 ( 23 )   11330 - 11338   2014年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A palladium-catalyzed and picolinamide-directed C-H thiolation of naphthylamine derivatives with diaryl disulfides has been developed to provide a convenient route to 8-sulfenyl-1-naphthylamines. The reaction proceeds via a 5-membered palladacycle intermediates to afford the peri-thiolated products exclusively, in contrast to the conventional ortho-functionalization. Moreover, the related direct selenation was also achieved with diaryl diselenides, giving the corresponding selenated products with perfect site-selectivity.

    DOI: 10.1021/jo502274t

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  • Iron-Induced Regio- and Stereoselective Addition of Sulfenyl Chlorides to Alkynes by a Radical Pathway 査読

    Masayuki Iwasaki, Tomoya Fujii, Kiyohiko Nakajima, Yasushi Nishihara

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   53 ( 50 )   13880 - 13884   2014年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    The radical addition of the ClS sigma-bond in sulfenyl chlorides to various CC triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal alkynes, internal alkynes underwent stereodefined chlorothiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via iron-mediated homolysis of the ClS bond. The resulting chlorothiolation adducts can be readily transformed to the structurally complex alkenyl sulfides by cross-coupling reactions. The present reaction can also be applied to the complementary synthesis of the potentially useful bis-sulfoxide ligands for transition-metal-catalyzed reactions.

    DOI: 10.1002/anie.201408121

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  • Chelate-Assisted Direct Selenation of Aryl C-H Bonds with Diselenides Catalyzed by Palladium 査読

    Masayuki Iwasaki, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

    ORGANIC LETTERS   16 ( 18 )   4920 - 4923   2014年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A direct selenation of inert C-H bonds of benzamide derivatives and their related compounds with diselenides has been achieved with the palladium catalyst. The reaction was compatible with a variety of functional groups, including a bromo group. Primitive mechanistic insights revealed that the reaction proceeded through a C H bond cleavage and the sequential oxidative addition of diselenides. The present synthetic method can be applied to the facile synthesis of selenoxanthone which can be regarded as promising heterocyclic materials.

    DOI: 10.1021/ol502439m

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  • Transistor Application of Phenacene Molecules and Their Characteristics

    Yoshihiro Kubozono, Xuexia He, Shino Hamao, Kazuya Teranishi, Hidenori Goto, Ritsuko Eguchi, Takashi Kambe, Shin Gohda, Yasushi Nishihara

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY   2014 ( 24 )   3806 - 3819   2014年8月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    The characteristics of field-effect transistors (FETs) fabricated from thin films and single crystals of phenacene molecules are fully reported in this review together with the electronic and crystal structures of phenacenes. Phenacene molecules possess a low HOMO level and a wide band gap. The highest mobility observed in the phenacene thin-film FETs is 7.4 cm(2)V(-1)s(-1) for [6]phenacene, and in single-crystal FETs the highest value is 6.3 cm(2)V(-1)s(-1) for [7]phenacene. The phenacene thin-film FETs show O-2-sensing properties unlike their single-crystal FETs. The bias-stress effect is fully investigated for phenacene single-crystal FETs. Furthermore, the low-voltage operation of phenacene single-crystal FETs with electric-double-layer (EDL) capacitors is reported. The temperature dependence of phenacene single-crystal FETs is reported to clarify the transport mechanism, which is suggestive of band-like transport.

    DOI: 10.1002/ejic.201402168

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  • New Entry to the Synthesis of α-Iminonitriles by Lewis Acid Mediated Isomerization of Cyano-Substituted Iminoisobenzofurans Prepared by Palladium-Catalyzed Three-Component Coupling of Arynes, Isocyanides, and Cyanoformates

    Jing Li, Shintaro Noyori, Kiyohiko Nakajima, Yasushi Nishihara

    Organometallics   33 ( 13 )   3500 - 3507   2014年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/om500408h

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  • Synthesis of 2,9-dialkylated phenanthro[1,2-b:8,7-b ']dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide 査読

    Keita Hyodo, Hikaru Nonobe, Shuhei Nishinaga, Yasushi Nishihara

    TETRAHEDRON LETTERS   55 ( 29 )   4002 - 4005   2014年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Phenanthro[1,2-b:8,7-b']dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b']dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents. (C) 2014 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2014.05.035

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  • Synthesis of Methoxy-Substituted Picenes: Substitution Position Effect on Their Electronic and Single-Crystal Structures

    Hiroki Mori, Xi-chao Chen, Ning-hui Chang, Shino Hamao, Yoshihiro Kubozono, Kiyohiko Nakajima, Yasushi Nishihara

    JOURNAL OF ORGANIC CHEMISTRY   79 ( 11 )   4973 - 4983   2014年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A series of picenes having methoxy groups was synthesized through Pd-catalyzed Suzuki-Miyaura couplings or Wittig reaction/intramolecular cyclization sequences, and their physicochemical properties and single-crystal structures were evaluated. The substitution position effects between the outer 1,12-, 2,11-, and 4,9-position and the inner 3,10-position are quite different; the former showed the same electronic structure as that of picene, but the latter results in a HOMO geometry different from those of picene and other methoxy picenes. In addition, crystal structures of four types of methoxy-substituted picenes 4a-c,e strongly depend on their substitution position and number of methoxy groups, which dramatically changes the structures from the fully anisotropic 1D pi-stacked structure to a unique 3D herringbone structure due to steric hindrance of methoxy groups. The calculations of transfer integrals based on their single-crystal structures reveal that the methoxy picenes have intermolecular overlaps less effective than that of the parent nonsubstituted picene. These results are attributed not only to the packing structure but also to electronic structures such as the HOMO distribution. The preliminary OFET of the representative 4c,e showed hole mobilities significantly lower than that of picene due to their less effective intermolecular overlaps, as predicted by the calculated transfer integrals.

    DOI: 10.1021/jo500543h

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  • Palladium- Catalyzed Direct Thiolation of Aryl C similar to H Bonds with Disulfides 査読

    Masayuki Iwasaki, Miki Iyanaga, Yuta Tsuchiya, Yugo Nishimura, Wenjuan Li, Zhiping Li, Yasushi Nishihara

    CHEMISTRY-A EUROPEAN JOURNAL   20 ( 9 )   2459 - 2462   2014年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    A catalytic variant of the direct thiolation of arenes, bearing directing groups, with disulfides or thiols has been developed under palladium and copper co-catalysis. Both sulfenyl moieties of the disulfide could be incorporated into the thiolated products, therefore, the reactions reached completion with only half an equivalent of disulfide, with respect to the starting arene. Experimental evidence suggested that the reaction proceeds through a Pd-II/Pd-IV mechanism.

    DOI: 10.1002/chem.201304717

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  • Palladium-Catalyzed Regio- and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides 査読

    Masayuki Iwasaki, Tomoya Fujii, Arisa Yamamoto, Kiyohiko Nakajima, Yasushi Nishihara

    CHEMISTRY-AN ASIAN JOURNAL   9 ( 1 )   58 - 62   2014年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.

    DOI: 10.1002/asia.201301295

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  • Diborylation of Alkynyl MIDA Boronates and Sequential Chemoselective Suzuki-Miyaura Couplings: A Formal Carboborylation of Alkynes 査読

    Keita Hyodo, Masato Suetsugu, Yasushi Nishihara

    ORGANIC LETTERS   16 ( 2 )   440 - 443   2014年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Platinum-catalyzed diborylation of phenylethynyl MIDA boronate with B-pin-B-pin proceeds to yield 1,1,2-triboryl-2-phenylethene with two different classes of the boron functionalities. Sequentially, the obtained 1,1,2-triboryl-2-phenylethene are subjected to Suzuki-Miyaura coupling to introduce a series of aryl groups chemoselectively to afford 1,1-boryl-2,2-diarylethenes.

    DOI: 10.1021/ol403326z

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  • Selective Synthesis of Multisubstituted Olefins Utilizing gem- and vic-Diborylated Vinylsilanes Prepared by Silylborylation of an Alkynylboronate and Diborylation of Alkynylsilanes 査読

    Jiao Jiao, Keita Hyodo, Hao Hu, Kiyohiko Nakajima, Yasushi Nishihara

    JOURNAL OF ORGANIC CHEMISTRY   79 ( 1 )   285 - 295   2014年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The synthesis of a series of gem- and vic-diborylated vinylsilanes was accomplished via highly selective transition-metal-catalyzed syn-dimetalation to the alkynylmetal species. This protocol served as a general synthetic method toward regio- and stereodefined multisubstituted olefins. The key steps are the diastereoselective Suzuki-Miyaura cross-coupling reactions of gem- and vic-diborylated vinylsilanes, in which the two boron groups showed discrete reactivities to afford diverse precursors of multisubstituted olefins.

    DOI: 10.1021/jo4024057

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  • Experimental and Theoretical Studies on the Platinum-Mediated Selective C(sp)-Si Bond Cleavage of Alkynylsilanes 査読

    奥田靖浩, 石黒雄也, 森 聖治, 中島清彦, 西原康師

    Organometallics   33   1878 - 1889   2014年

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    記述言語:英語  

    DOI: 10.1021/om5002588

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  • The origin of exo-selectivity in methyl cyanoformate addition onto the C=C bond of norbornene in Pd-catalyzed cyanoesterification” 査読

    奥田靖浩, Szilagyi, R. K, 森 聖治, 西原康師

    Dalton Trans.   43   9537 - 9548   2014年

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    記述言語:英語  

    DOI: 10.1039/c4dt00839a

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  • Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3 査読

    李 靖, 奥田靖浩, 趙 家冀, 森 聖治, 西原康師

    Org. Lett.   16   5220 - 5223   2014年

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    記述言語:英語  

    DOI: 10.1021/ol5026519

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  • Phenanthro[1,2-b:8,7-b']dithiophene: A new picene-type molecule for rransistor applications 査読

    西原康師, 木下 恵, 兵頭恵太, 奥田靖浩, 江口律子, 後藤秀徳, 浜尾志乃, 高林康裕, 久保園 芳博

    RSC Advances   3   19341 - 19347   2014年

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    記述言語:英語  

    DOI: 10.1039/c3ra44050h

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  • Synthesis, structure, and isomerization of alkoxycarbonyl(chloro)(cyano)rhodium(III) complexes, mer- RhCl(CO2R)(CN)(PMe3)3 (R = Me, Et, nPr, iPr, nBu, and Bn) through C–C bond cleavage of cyanoformates 査読

    奥田靖浩, 岡本 尊, 山本有沙, 李 靖, 中島清彦, 西原康師

    Chem. Lett.   43   417 - 419   2014年

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    記述言語:英語  

    DOI: 10.1246/cl.131072

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  • Palladium-Catalyzed Annulation of o-lodobiphenyls with o-Bromobenzyl Alcohols: Synthesis of Functionalized Triphenylenes via C-C and C-H Bond Cleavages 査読

    Masayuki Iwasaki, Shohel Lino, Yasushi Nishihara

    ORGANIC LETTERS   15 ( 20 )   5326 - 5329   2013年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Treatment of o-iodobiphenyls with abromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C-C bond formations and C-C and C-H bond cleavages. A combination of palladium and an electron-deficient phosphine ligand proves to be effective for both decarbonylative cross-coupling and intramolecular cyclization.

    DOI: 10.1021/oI4025869

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  • Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Silylborylation of an Alkynylboronate/Chemoselective Cross-Coupling Sequences 査読

    Jiao Jiao, Kiyohiko Nakajima, Yasushi Nishihara

    ORGANIC LETTERS   15 ( 13 )   3294 - 3297   2013年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A highly regio- and stereoselective silylborylation of an alkynylboronate is disclosed. PhMe2Si-B-pin undergoes a Pd(OAc)(2)/(t)OctNC-catalyzed syn-addition to the alkynylboronate to yield 1-phenyl-1-silyl-2,2-diborylethene with high regioselectivity. The product 1-phenyl-1-silyl-2,2-diborylethene is then chemoselectively arylated by Suzuki-Miyaura coupling to afford (2)-1-silyl-2-borylstilbene derivatives. This approach is extended to the synthesis of a tetraarylated olefin with four different substituents.

    DOI: 10.1021/ol401333j

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  • Synthesis of cyclic 1-alkenylboronates via Zr-mediated double functionalization of alkynylboronates and sequential Ru-catalyzed ring-closing olefin metathesis 査読

    Yasushi Nishihara, Masato Suetsugu, Daisuke Saito, Megumi Kinoshita, Masayuki Iwasaki

    Organic Letters   15 ( 10 )   2418 - 2421   2013年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    Synthesis of novel cyclic 1-alkenylboronates is accomplished through the zirconium-mediated regio- and stereoselective double functionalization of 1-alkynylboronates and the subsequent ruthenium-catalyzed ring-closing metathesis (RCM). The obtained substituted cyclic 1-alkenylboronates are transformed into o-terphenyl and triphenylene derivatives. © 2013 American Chemical Society.

    DOI: 10.1021/ol400896u

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  • Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: efficient synthetic methods for diaryl ketones and chalcones at room temperature 査読

    Daisuke Ogawa, Keita Hyodo, Masato Suetsugu, Jing Li, Yoshiaki Inoue, Mamoru Fujisawa, Masayuki Iwasaki, Kentaro Takagi, Yasushi Nishihara

    TETRAHEDRON   69 ( 12 )   2565 - 2571   2013年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or chalcones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible. (C) 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2013.01.058

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  • Palladium-free synthesis of unsymmetrical diarylethynes by cross-coupling reaction of alkynylboronates with aryl iodides catalyzed by CuCl 査読

    Daisuke Ogawa, Jing Li, Masato Suetsugu, Jiao Jiao, Masayuki Iwasaki, Yasushi Nishihara

    TETRAHEDRON LETTERS   54 ( 6 )   518 - 521   2013年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A series of unsymmetrical diarylethynes have been synthesized by the copper-catalyzed cross-coupling reaction of alkynylboronates with aryl iodides in high to excellent yields under palladium-free conditions. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible with this reaction. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2012.11.069

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  • Synthesis of substituted [6]phenacenes through Suzuki–Miyaura coupling of polyhalobenzene with alkenylboronates and sequential intramolecular cyclization via C–H bond activation 査読

    常 寧輝, 森 裕樹, 陳 璽朝, 奥田靖浩, 岡本 尊, 西原康師

    Chem. Lett.   42   1257 - 1259   2013年

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    記述言語:英語  

    DOI: 10.1246/cl.130584

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  • Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties 査読

    常 寧輝, 陳 璽朝, 野々部 瑛, 奥田靖浩, 森 裕樹, 中島清彦, 西原康師

    Org. Lett.   15   3558 - 3561   2013年

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    記述言語:英語  

    DOI: 10.1021/ol401375n

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  • A NOVEL THREE-COMPONENT COUPLING REACTION OF ARYNES, ISOCYANIDES, AND CYANOFORMATES: A STRAIGHTFORWARD ACCESS TO CYANO-SUBSTITUTED IMINOISOBENZOFURANS 査読

    Jing Li, Shintaro Noyori, Masayuki Iwasaki, Kiyohiko Nakajima, Yasushi Nishihara

    HETEROCYCLES   86 ( 2 )   933 - 940   2012年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Iminoisobenzofuran derivatives have been prepared in moderate yields by the palladium-catalyzed three-component coupling reaction of arynes, isocyanides, and cyanoformates. This paper is dedicated to Professor Ei-ichi Negishi on the occasion of his 77th birthday.

    DOI: 10.3987/COM-12-S(N)77

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  • Synthesis of Unsymmetrical Diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira-Hagihara Coupling Reactions of Alkynylsilanes with Aryl Tosylates or Mesylates 査読

    Yasushi Nishihara, Daisuke Ogawa, Shintaro Noyori, Masayuki Iwasaki

    CHEMISTRY LETTERS   41 ( 11 )   1503 - 1505   2012年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Palladium/copper-cocatalyzed cross-coupling reactions of alkynylsilanes with aryl tosylates or mesylates afforded the corresponding unsymmetrical diarylethynes in moderate to good yields. The optimized reaction conditions to afford higher yields of cross-coupled products were found to be 5 mol % of [PdCl2(bpy)], 15 mol % of BrettPhos, and 10 mol % of (CuCl)-Cl-I in DMF as a solvent.

    DOI: 10.1246/cl.2012.1503

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  • Synthesis of unsymmetrically disubstituted ethynes by the palladium/copper(I)-cocatalyzed sila-Sonogashira-Hagihara coupling reactions of alkynylsilanes with aryl iodides, bromides, and chlorides through a direct activation of a carbon-silicon bond 査読

    Yasushi Nishihara, Eiji Inoue, Shintaro Noyori, Daisuke Ogawa, Yoshiaki Okada, Masayuki Iwasaki, Kentaro Takagi

    TETRAHEDRON   68 ( 24 )   4869 - 4881   2012年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    In this paper, we explore the copper/palladium-cocatalyzed cross-coupling reactions of 1-aryl-2-trimethylsilylethynes with aryl iodides, bromides, and chlorides as coupling partners, to furnish unsymmetrically disubstituted ethynes in moderate to excellent yields. Various aryl iodides were subjected to reaction under the optimized conditions with 5 mol % of Pd(PPh3)(2) and 50 mol % of CuCl. The steric properties of the aryl iodide proved more influential to the outcome of the cross-coupling reaction than electronic factors. In addition, we succeeded in synthesizing unsymmetrical diarylethynes using two different aryl iodides in one-pot. Furthermore, under the same reaction conditions with 10 mol % of PdCl2, 40 mol % of P(4-FC6H4)(3), and 50 mol % of CuCl as catalyst, we succeeded in synthesizing unsymmetrical diarylethynes from various aryl bromides. Finally, we explored reactions with aryl chlorides and duly discovered that unsymmetrical diarylethynes were obtainable in moderate to good yields when 10 mol % of Pd(OAc)(2), 10 mol % of (-)-DIOP, and 10 mol % of CuCl were used. These reactions proceed through a direct activation of a carbon silicon bond in alkynylsilanes by CuCl to generate the corresponding alkynylcopper species via transmetalation from silicon to copper. Mechanistic investigations on the reaction of alkynylsilanes with aryl bromides confirmed that the trimethylsilyl bromide generated in situ retarded both transmetalation steps between CuCl and alkynylsilane, and between palladium(II) species formed by oxidative addition and alkynylcopper species. (C) 2012 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2012.03.093

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  • Iron-Catalyzed Oxidation of Tertiary Amines: Synthesis of beta-1,3-Dicarbonyl Aldehydes by Three-Component C-C Couplings 査読

    Weiping Liu, Jinhua Liu, Daisuke Ogawa, Yasushi Nishihara, Xingwei Guo, Zhiping Li

    ORGANIC LETTERS   13 ( 23 )   6272 - 6275   2011年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    beta-1,3-Dicarbonyl aldehydes were synthesized by iron-catalyzed oxidative reactions between 1,3-dicarbonyl compounds and two molecules of tertiary amines in the presence of tert-butyl hydroperoxide (TBHP). alpha,beta-Unsaturated aldehydes generated by tertiary amine oxidation In situ act as key intermediates under mild reaction conditions.

    DOI: 10.1021/ol202749x

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  • Copper-catalyzed Sila-Sonogashira-Hagihara Cross-coupling Reactions of Alkynylsilanes with Aryl Iodides under Palladium-free Conditions

    Yasushi Nishihara, Shintaro Noyori, Takeru Okamoto, Masato Suetsugu, Masayuki Iwasaki

    CHEMISTRY LETTERS   40 ( 9 )   972 - 974   2011年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    An efficient and inexpensive catalytic system using a readily available CuCl/PPh3 combination for the catalytic cross-coupling reactions of alkynylsilanes with a variety of aryl iodides affords unsymmetrical diarylethynes in good to excellent yields.

    DOI: 10.1246/cl.2011.972

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  • Rh-Catalyzed Carbonylation of Arylzinc Compounds Yielding Symmetrical Diaryl Ketones by the Assistance of Oxidizing Agents

    Kana Kobayashi, Yugo Nishimura, Fuxing Gao, Kazuma Gotoh, Yasushi Nishihara, Kentaro Takagi

    JOURNAL OF ORGANIC CHEMISTRY   76 ( 6 )   1949 - 1952   2011年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Carbonylative homocoupling of arylzinc compounds 1 using 1 atm of CO and 1,2-dibromoethane as an oxidant was achieved in the presence of Rh-dppf catalyst, affording symmetrical diaryl ketones in good yields. Under similar conditions, Pd or Ni catalysts induced oxidative homo coupling of 1 to yield biaryls instead. The beneficial catalysis by Rh in the carbonylation was presumed to stem from the facility by which the migration of the aryl ligand to CO at the Rh3+ intermediate occurred.

    DOI: 10.1021/jo1025173

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  • Improvement in sulfur desorption of NOX storage and reduction catalysts using a Ba-Ti composite oxide

    Toshiyuki Tanaka, Ichirou Tajima, Yuichi Kato, Yasushi Nishihara, Hirofumi Shinjoh

    APPLIED CATALYSIS B-ENVIRONMENTAL   102 ( 3-4 )   620 - 626   2011年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    A Ba-Ti composite oxide was formed on a NOx storage and reduction catalyst via impregnation of a Ba-Ti precursor solution composed of H2O2 added to a complex prepared using the citric acid method. The structure of the Ba-Ti composite in solution was analyzed by chemical composition analysis and FT-Raman and UV-vis spectroscopy. MM2 calculations were performed to propose its chemical structure. Both Ba and Ti together were found to form a composite molecule in the solution. Furthermore, TEM-EDX and XRD analyses of the Ba-Ti composite oxide on the catalyst prepared by impregnation with the Ba-Ti composite aqueous solution revealed that Ba and Ti in the catalyst were highly dispersed at the nm scale. The formation of the Ba-Ti composite oxide on the NSR catalyst enhanced sulfur desorption efficiency and led to high-performance NOX conversion as a NOX storage and reduction activity catalyst after desulfation treatment. It was assumed that the existence of nano-scaled Ba compounds combined with Ti was efficient for the inhibition of the sintering of barium sulfate and its facile decomposition. It was found that dispersion of Ba compounds for NOX storage materials using a Ba-Ti complex solution is an efficient way to improve the durability of NSR catalysts. (C) 2011 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.apcatb.2011.01.002

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  • Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki-Miyaura Coupling Reactions

    Yasushi Nishihara, Yoshiaki Okada, Jiao Jiao, Masato Suetsugu, Ming-Tzu Lan, Megumi Kinoshita, Masayuki Iwasaki, Kentaro Takagi

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 37 )   8660 - 8664   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-BLACKWELL  

    DOI: 10.1002/anie.201103601

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  • Negishi Alkyl-Aryl Cross-Coupling Catalyzed by Rh: Efficiency of Novel Tripodal 3-Diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl Acetate Ligand

    Syogo Ejiri, Shunsuke Odo, Hideki Takahashi, Yugo Nishimura, Kazuma Gotoh, Yasushi Nishihara, Kentaro Takagi

    ORGANIC LETTERS   12 ( 8 )   1692 - 1695   2010年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    3-Diphenylphosphino-2-(diphenylphoshino)methyl-2-methylpropyl acetate acted as an efficient ligand for a Rh catalyst, achieving cross-coupling between arylzinc compounds bearing electron-withdrawing groups and alkyl electrophiles. The beneficial effect of the tripodal ligand and such aryl nucleophiles was discussed with regard to the specificity of the Rh catalysis.

    DOI: 10.1021/ol100210u

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  • Enantioseparation of Doubly Functionalized Polar Norbornenes by HPLC and Their Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization

    Yasushi Nishihara, Yukiko Doi, Seisuke Izawa, Horng-Yi Li, Yoshiaki Inoue, Masaaki Kojima, Jwu-Ting Chen, Kentaro Takagi

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   48 ( 2 )   485 - 491   2010年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:JOHN WILEY & SONS INC  

    DOI: 10.1002/pola.23781

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  • Palladium- and base-free synthesis of conjugated ynones by cross-coupling reactions of alkynylboronates with acid chlorides mediated by CuCl

    Yasushi Nishihara, Daisuke Saito, Eiji Inoue, Yoshiaki Okada, Mikihiro Miyazaki, Yoshiaki Inoue, Kentaro Takagi

    TETRAHEDRON LETTERS   51 ( 2 )   306 - 308   2010年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Alkynylboronates can be employed as a practical and versatile precursor for a variety of pi-conjugated organic compounds. In the presence of Cu(I) salt, cross-coupling reactions of acid chlorides with alkynylboronates giving rise to the corresponding conjugated ynones takes place readily in aprotic polar solvents such as DMI under neutral conditions. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.11.001

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  • Development of New Methodology for Bond Activation by Transition Metal Complexes and Their Application toward Functional Molecule Synthesis

    Yasushi Nishihara

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   67 ( 9 )   889 - 897   2009年9月

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    記述言語:日本語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SOC SYNTHETIC ORGANIC CHEM JPN  

    In this review, the results of studies on new methodology for bond activation by using transition metal complexes are described, in order to realize the expeditious and selective synthesis of organic compounds. Carbon-carbon bond formation reactions, accompanying with cleavage of unactivated bonds such as carbon-carbon, carbon-boron, and carbon-silicon bonds, are reported. This review involves, for examples, the new synthetic methodology to introduce both cyano and ester groups (cyanoesterification) via the C-C bond activation, regio- and stereoselective synthesis multi-substituted olefins mediated a zirconocene complex via the C-B bond activation, and cross-coupling reaction of alkynylsilanes activated by a copper salt via the C-Si bond cleavage. Each reaction can be applicable to synthesis of functional molecules such as opto-electronic materials, an anti-cancer agent, and liquid crystalline compounds.

    DOI: 10.5059/yukigoseikyokaishi.67.889

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  • Palladium/copper-catalyzed sila-Sonogashira reactions of aryl iodides with alkynylsilanes via a direct C-Si bond activation

    Yasushi Nishihara, Eiji Inoue, Daisuke Ogawa, Yoshiaki Okada, Shintaro Noyori, Kentaro Takagi

    TETRAHEDRON LETTERS   50 ( 32 )   4643 - 4646   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The palladium-catalyzed cross-coupling reactions of aryl iodides with alkynylsilanes in the presence of a substoichiometric amount (50 mol %) of copper(I) chloride as an activator in DMF under strictly non-basic reaction conditions afford the corresponding unsymmetrical diarylethynes in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.05.112

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  • Regio- and Stereoselective Synthesis of Multisubstituted Vinylsilanes via Zirconacycles

    Yasushi Nishihara, Daisuke Saito, Kenki Tanemura, Shintaro Noyori, Kentaro Takagi

    ORGANIC LETTERS   11 ( 16 )   3546 - 3549   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A series of novel multisubstituted vinylsilanes are prepared regio- and stereoselectively by carbozirconation of various alkynylsilanes through zirconacycles such as zirconacyclopropenes and zirconacyclopentenes and the subsequent transformation of the formed alkenylzirconocene complexes.

    DOI: 10.1021/ol901236s

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  • Comparative reactivity of triorganosilanes, HSi(OEt)(3) and HSiEt3, with IrCl(CO)(PPh3)(2). Formation of IrCl(H)(2)(CO)(PPh3)(2) or Ir(H)(2)(SiEt3)(CO)(PPh3)(2) depending on the substituents at Si

    Yasushi Nishihara, Miwa Takemura, Kohtaro Osakada

    INORGANICA CHIMICA ACTA   362 ( 8 )   2951 - 2956   2009年6月

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    記述言語:英語   出版者・発行元:ELSEVIER SCIENCE SA  

    Reaction of HSi(OEt)(3) with IrCl(CO)(PPh3)(2) (5:1 molar ratio) at room temperature for 1 h gives IrCl(H){Si(OEt)(3)}(CO)(PPh3)(2) (1), which is observed by the H-1 and P-31{H-1} NMR spectra of the reaction mixture. The same reaction, but in 20:1 molar ratio at 50 degrees C for 24 h produces IrCl(H)(2)(CO)(PPh3)(2) (2) rather than the expected product Ir(H)(2){Si(OEt)(3)}(CO)(PPh3)(2) (3) that was previously reported to be formed by this reaction. Accompanying formation of Si(OEt)(4), (EtO)(3)SiOSi(OEt)(3), and (EtO)(2)HSiOSi(OEt)(3) is observed. On the other hand, trialkylhydrosilane HSiEt3 reacts with IrCl(CO)(PPh3)(2) (10:1 molar ratio) at 80 degrees C for 84 h to give Ir(H)(2)(SiEt3)(CO)(PPh3)(2) (4) in a high yield, accompanying with a release of ClSiEt3. (C) 2009 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.ica.2008.12.033

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  • Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to alpha- or beta-Phosphoryl-Substituted Alkylarenes

    Hideki Takahashi, Shinya Inagaki, Naoko Yoshii, Fuxing Gao, Yasushi Nishihara, Kentaro Takagi

    JOURNAL OF ORGANIC CHEMISTRY   74 ( 7 )   2794 - 2797   2009年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The catalytic cross-coupling between ArZnX and ICH(2)(CH(2))(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, P-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.

    DOI: 10.1021/jo900142b

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  • Photocatalytic Activities of Graphitic Carbon Nitride Powder for Water Reduction and Oxidation under Visible Light

    Kazuhiko Maeda, Xinchen Wang, Yasushi Nishihara, Daling Lu, Markus Antonietti, Kazunari Domen

    JOURNAL OF PHYSICAL CHEMISTRY C   113 ( 12 )   4940 - 4947   2009年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Graphitic carbon nitride (g-C(3)N(4)) with a band gap of 2.7 eV is studied as a nonmetallic photocatalyst for H(2) or O(2) evolution from water under ultraviolet (UV) and visible light. The g-C(3)N(4) catalyst exhibits activities for water reduction into H(2) or water oxidation into O(2) in the presence of a proper sacrificial electron donor or acceptor, respectively, even without the need for precious metal cocatalysts. When bis(1,5-cyclooctadiene)platinum complex [Pt(cod)(2)] (a nonionic complex) is used as a precursor of Pt cocatalyst instead of H(2)PtCl(6) (an ionic complex), enhanced H(2)) evolution activity is acquired. This difference in activity is primarily due to the better dispersion of Pt nanoparticles on g-C(3)N(4), which is considered to originate from the better access of Pt(cod)(2) to the g-C(3)N(4) surface, as compared to that of H(2)PtCl(6) in the preparation process. Unmodified g-C(3)N(4) produces O(2) from an aqueous silver nitrate solution upon UV irradiation (lambda > 300 nm), although N(2), release due to self-decomposition of g-C(3)N(4) by photogenerated holes takes place. Modification of g-C(3)N(4) with RuO(2), improves not only O(2) evolution activity but also stability against the self-decomposition, resulting in stable visible-light-driven O(2) evolution (lambda > 420 nm).

    DOI: 10.1021/jp809119m

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  • Synthesis and Ion Conductive Characteristics of Inorganic-Organic Hybrid Polymers Bearing a Tetraarylpentaborate Unit

    Yasushi Nishihara, Mikihiro Miyazaki, Yasumasa Tomita, Yuuki Kadono, Kentaro Takagi

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   46 ( 23 )   7913 - 7918   2008年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:JOHN WILEY & SONS INC  

    DOI: 10.1002/pola.23070

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  • Sila-Sonogashira Cross-Coupling Reactions of Activated Aryl Chlorides with Alkynylsilanes

    Yasushi Nishihara, Eiji Inoue, Yoshiaki Okada, Kentaro Takagi

    SYNLETT   ( 19 )   3041 - 3045   2008年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    The palladium/copper-cocatalyzed sila-Sonogashira cross-coupling reactions of activated aryl chlorides with alkynylsilanes under strictly nonbasic conditions yield the unsymmetrical diarylethynes in moderate to good yields.

    DOI: 10.1055/s-0028-1087345

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  • Synthesis, characterization, and thermal properties of ring-opening metathesis polynorbornenes and their hydrogenated derivatives bearing various ester and cyano groups

    Yasushi Nishihara, Seisuke Izawa, Yoshiaki Inoue, Yuushou Nakayama, Takeshi Shiono, Kentaro Takagi

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   46 ( 10 )   3314 - 3325   2008年5月

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    記述言語:英語   出版者・発行元:JOHN WILEY & SONS INC  

    Doubly functionalized polar norbornenes 3a-3g substituted by both a variety of ester and cyano groups were polymerized by ring-opening metathesis polymerization (ROMP) with a Ru carbene complex 2 bearing 3-bromopyridine as a ligand (third generation Grubbs' catalyst) in a living manner. The successive hydrogenation of the main-chain double bond in the synthesized living ROMP polymers 4a-4g with a hydridoruthenium complex was exploited. The comparison of thermal properties of a series of ring-opening metathesis polymers 4a-4g with those of their hydrogenated derivatives 5a-5g revealed the decrease of glass transition temperatures (T-g) but little change of the 5% decomposition temperature (T-d(5)). In all cases examined in this study, a decrease of T-g by hydrogenation was around 20-40 degrees C, regardless of the ester substitutents. In the presence of the additional PCy3, triethylamine, and methanol after complete consumption of monomer 3a under the living ROMP condition, the tandem ROMP-hydrogenation of the resulting polymer 4a generated in situ was attained under a H-2 (9.8 MPa) atmosphere at 80 degrees C to afford the hydrogenated polymer 5a, retaining the narrow polydispersity of 1.03. (C) 2008 Wiley Periodicals, Inc.

    DOI: 10.1002/pola.22671

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  • Pd-P(t-BU)(3)-catalyzed consecutive cross-coupling of p-phenylenedizinc compound with two different electrophiles leading to unsymmetrically 1,4-disubstituted benzenes

    Takahiro Kawamoto, Shogo Ejiri, Kana Kobayashi, Shunsuke Odo, Yasushi Nishihara, Kentaro Takagi

    JOURNAL OF ORGANIC CHEMISTRY   73 ( 4 )   1601 - 1604   2008年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

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    Pd-P(t-BU)(3) was found to be a chemoselective catalyst for the reaction of p-phenylenedizinc compound with equimolar amounts of carbon electrophiles to afford the single cross-coupling products in good yields, effectively suppressing the formation of double cross-coupling products. The subsequent additions of other electrophiles to the resulting solutions caused the second cross-coupling of the incipient products to take place, achieving a novel and efficient one-pot synthesis of unsymmetrically 1,4-disubstituted benzenes. The origin of the observed high chemoselectivity was speculated.

    DOI: 10.1021/jo702103r

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  • Zirconocene-mediated highly regio- and stereoselective synthesis of multisubstituted olefins starting from 1-alkynylboronates 査読

    Yasushi Nishihara, Mitsuru Miyasaka, Masanori Okamoto, Hideki Takahashi, Eiji Inoue, Kenki Tanemura, Kentaro Takagi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   129 ( 42 )   12634 - +   2007年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Multisubstituted olefins are efficiently prepared by the zirconocene-mediated regio- and stereoselective coupling between 1alkynylboronates and ethylene, followed by sequential transformation in moderate to high yields. The proper combination of substrates and reaction conditions is important for high yields. The synthesis of various tetra substituted alkenes in a regio- and stereocontrolled manner is described. This methodology has been applied to the synthesis of (Z )-tamoxifen in a concise, regio and stereoselective manner. This multicomponent coupling strategy involves the characteristics of 1-alkynylboronates toward high selectivities followed by palladium(O)-mediated cross-coupling with aryl halides.

    DOI: 10.1021/ja075234y

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  • Preparation, structures, and thermal reactivity of alkoxycarbonyl(cyano)palladium(II) complexes trans-Pd(COOR)(CN)(PPh3)(2) (R = Me, Et, Pr-n, Pr-i, Bu-n, Bu-t, and Bn) as intermediates of the palladium-catalyzed cyanoesterification of norbornene derivatives

    Yasushi Nishihara, Mitsuru Miyasaka, Yoshiaki Inoue, Tomoka Yamaguchi, Masaaki Kojima, Kentaro Takagi

    ORGANOMETALLICS   26 ( 16 )   4054 - 4060   2007年7月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    Alkoxycarbonyl(cyano)palladium(II) complexes trans-Pd(COOR)(CN)(PPh3)(2) (1, R = Me; 2, R = Et; 3, R = Pr-n; 4, R = Pr-i; 5, R = Bu-n; 6, R = Bu-t; 7, R = Bn) are prepared via oxidative addition of the corresponding cyanoformates to Pd(PPh3)(4) in toluene at room temperature or 50 degrees C and characterized by means of NMR (H-1, C-13{H-1}, and P-31{H-1}) and IR spectroscopy as well as elemental analyses. X-ray crystallography of 3, 4, and 6 showed a square-planar coordination around the Pd center that is bonded to alkoxycarbonyl and cyano ligands in the trans configuration. The Pd-CN and Pd-COOR bonds in 1, 3, 4, and 6 are similar to those of the cyanopalladium(II) and alkoxycarbonylpalladium(II) complexes reported to date. On reaction of Pd(PPh3)(4) with phenyl cyanoformate a thermally induced ligand exchange takes place to afford the dicyanopalladium(II) complex, trans-Pd(CN)(2)(PPh3)(2) (8). Complex 2 is able to catalyze the reaction of norbornadiene with ethyl cyanoformate to produce (2R*,3S*)-ethyl 3-cyanobicyclo[2.2.1]hept-5-ene-2-carboxylate (13) and is recovered after the reaction. This observation supports the identification of alkoxycarbonyl(cyano)palladium(II) complexes as intermediates in the catalytic cycle of cyanoesterification of norbornene derivatives.

    DOI: 10.1021/om700343y

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  • 1,1,3,3-Tetrakis(alkylthio)-1,3-dilithio-2-silapropanes: useful reagents for the synthesis of polysilacycloalkanes via dianionic ring formation

    Masaki Shimizu, Masayuki Iwakubo, Yasushi Nishihara, Katsunari Oda, Tamejiro Hiyama

    ARKIVOC   29 - 48   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ARKAT USA INC  

    Treatment of 1,1,3,3-tetrakis(alkylthio)-2-silapropanes with t-BuLi in THF at -40 degrees C generated 1,1,3,3-tetrakis(alkylthio)-1,3-dilithio-2-silapropanes which reacted with various bifunctional chlorosilanes to give the corresponding 4- to 7-membered polysilacycloalkanes in moderate to good yields. Furthermore, double alkylation of the dilithiated silanes with bis(halomethyl)diorganosilanes or dihaloalkanes was found to proceed smoothly giving rise to 1,4-disilacyclohexanes or silacycloalkanes in good yields, respectively, in THF and an aprotic polar co-solvent such as hexamethylphosphoric triamide (HMPA) or 1,1,3,3-tetramethylurea (TMU). The sulfenyl groups in the cyclized products were smoothly removed by radical reduction with tributyltin hydride.

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  • Living ring-opening metathesis polymerization of Exo-norbornenes bearing both cyano and ester functionalities by a well-defined ruthenium catalyst

    Yasushi Nishihara, Yoshiaki Inoue, Akira T. Saito, Yuushou Nakayama, Takeshi Shiono, Kentaro Takagi

    POLYMER JOURNAL   39 ( 4 )   318 - 329   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SOC POLYMER SCIENCE JAPAN  

    Exo-ethyl 3-cyanobicyclo[2.2.1]hept-5-ene-2-carboxylate (A) and exo-(n)butyl 3-cyanobicyclo[2.2.1]-hept-5-ene-2-carboxylate (B) bearing both cyano and ester groups were subjected to homopolymerization by ring-opening metathesis polymerization with a well-defined Ru catalyst, (H(2)IMes)(3-bromopyridine)(2)Cl2Ru=CHPh (3) (H(2)IMes = N,N'-bis(mesityl)-4,5-dihydroimidazol-2-ylidine) at low temperature. The characterization of the synthesized homopolymers by GPC analyses showed a value of a number-average molecular weight (Mn) as high as 296,000 and a narrow polydispersity index (< 1.06). The results imply that the initiator 3 had a compatibility of the polar functional groups and promoted fairly well-defined living polymerization. The glass transition temperatures of the homopolymers obtained from monomer A were significantly higher than those observed for polymers from monomer B obtained under the same reaction conditions. The rates of homopolymerizations of monomer A, B, and the parent norbornene (C) were determined by the monitoring the consumption of the monomers by the H-1 NMR spectra. It was revealed that the polymerization rate for the homopolymerization of monomer A was almost same as that of monomer B, but much slower than that of C. On the basis of the successful homopolymerization, the synthesis of block and random copolymers derived from monomers A, B, and C via living polymerization using catalyst 3 was also accomplished.

    DOI: 10.1295/polymj.PJ2006129

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  • Cyanoesterification of norbornenes catalyzed by palladium: facile synthetic methodology to introduce cyano and ester functionalities via direct carbon-carbon bond cleavage of cyanoformates

    Yasushi Nishihara, Yoshiaki Inoue, Seisuke Izawa, Mitsuru Miyasaka, Kenki Tanemura, Kiyohiko Nakajima, Kentaro Takagi

    TETRAHEDRON   62 ( 42 )   9872 - 9882   2006年10月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Addition of cyanoformates (NC-COOR) to norbornene at 110 degrees C in the presence of Pd(PPh(3))(4) (10 mol %) as a catalyst affords with high selectivity the corresponding doubly functionalized polar norbornane derivatives bearing both cyano and ester groups. By using benzonorbornadiene and norbornadienes as the substrates, the reaction can be extended to synthesis of various functionalized norbornene derivatives in moderate to excellent yields. In most cases alkyl groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert-butyl, and benzyl in the ester functionalities are applicable to the reactions. Oxidative addition of cyanoformates to Pd(0), insertion of norbornenes, and reductive elimination of the corresponding adducts constitute the proposed catalysis pathway. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2006.08.025

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  • Comparative reactivity of exo- and endo-isomers in the Ru-initiated ring-opening metathesis polymerization of doubly functionalized norbornenes with both cyano and ester groups

    Yasushi Nishihara, Yoshiaki Inoue, Yuushou Nakayama, Takeshi Shiono, Kentaro Takagi

    MACROMOLECULES   39 ( 22 )   7458 - 7460   2006年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ma061781c

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  • Novel Rh catalysis in cross-coupling between alkyl halides and arylzinc compounds possessing ortho-COX (X = OR, NMe2, or Ph) groups

    Hideki Takahashi, Shinya Inagaki, Yasushi Nishihara, Takanori Shibata, Kentaro Takagi

    ORGANIC LETTERS   8 ( 14 )   3037 - 3040   2006年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    Rh-dppf was found to be an efficient catalyst for the cross-coupling between primary alkyl halides bearing beta-hydrogens and arylzinc compounds possessing carbonyl groups such as ester, amide, or ketone at the ortho position. Various functional groups such as ester, nitrile, or acyloxylate moieties on the halides were tolerated under the catalysis conditions. Arylzinc compounds free of ortho-carbonyl groups reacted well with ethyl 3-iodopropanoate, suggesting that the essential intramolecular interaction between carbonyl groups and Rh promotes the reductive elimination.

    DOI: 10.1021/ol060969d

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  • Synthesis of functionalized benzylsilanes from arylzinc compounds and (iodomethyl)trimethylsilane by means of a novel Rh catalysis

    H Takahashi, KM Hossain, Y Nishihara, T Shibata, K Takagi

    JOURNAL OF ORGANIC CHEMISTRY   71 ( 2 )   671 - 675   2006年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.

    DOI: 10.1021/jo0520994

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  • Synthesis of symmetrical 1,3-butadiynes by homocoupling reactions of alkynylboronates mediated by a copper salt

    Y Nishihara, M Okamoto, Y Inoue, M Miyazaki, M Miyasaka, K Takagi

    TETRAHEDRON LETTERS   46 ( 50 )   8661 - 8664   2005年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Alkynylboronates are employed as a practical and versatile precursor for a variety of it-conjugated organic compounds. In the presence of a Cu(I) or Cu(II) salt, transformation of alkynylboronates into the corresponding 1,3-diynes upon exposure to air takes place readily in aprotic polar solvents such as DMI. (c) 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2005.10.056

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  • Ring-opening isomerization of methylenecyclopropanes catalyzed by hydridorhodium(I) complexes

    M Itazaki, Y Nishihara, H Takimoto, C Yoda, K Osakada

    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL   241 ( 1-2 )   65 - 71   2005年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE BV  

    2-Phenyl-1-methylenecyclopropane is isometized into 2-phenyl-1,3-butadiene and 1-phenyl-1,3-butadiene in the presence of catalytic amounts of RhH(CO)(PPh3)(3) and RhH(PPh3)(4). The Rh-containing product of the reactions has a 2-phenyl-1-methylallyl (or 1-phenyl-1-methylallyl) ligand, and is formed also from the reaction of 2-phenyl-1,3-butadiene with RhH(CO)(PPh3)(3). RhH(CO)(PPh3)(3) promotes ring-opening isomerization of 4-phenyl-1-methylenespiro[2,2]pentane to afford Rh[eta(3)-anti-CH2C{C(=CH2)Ph}CHCH3](PPh3)(2) (2) at 50 degrees C and Rh{kappa(1),eta(2)-CH2CH(Ph)C(=CH2)CH=CH2}(CO)(PPh3)(2) (3) at -35 degrees C. X-ray crystallography of 2 shows the pi-allylic ligand having a methyl group at anti position. The mechanism for formation of 2 via intermediate 3 is discussed. (c) 2005 Elsevier B.V All rights reserved.

    DOI: 10.1016/j.molcata.2005.06.045

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  • Preparation of Pd(PPh2H)(2)(PPh3)(2) and its role as a precursor of a dinuclear complex with bridging phosphide ligands

    M Itazaki, Y Nishihara, K Osakada

    TRANSITION METAL CHEMISTRY   30 ( 7 )   828 - 830   2005年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:SPRINGER  

    Reaction of PPh2H with Pd(PPh3)(4) in a 4:1 molar ratio produced the Pd complex with two diphenylphosphine ligands, Pd(PPh2H)(2)(PPh3)(2) (1). Complex (1) was characterized by n.m.r. (H-1 and P-31{H-1}) spectra as well as by elemental analysis. Reaction of (1) with RhCl(PPh3)(3) yielded a Pd-Rh heterobimetallic complex with bridging phosphide ligands, formulated as [(Ph3P)(2)Pd(mu-PPh2)(2)Rh(PPh3)(2)]Cl (2).

    DOI: 10.1007/s11243-005-6408-x

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  • Hexanuclear Pt complexes composed of two cyclic triplatinum units connected with 1,4-diphenylene and 1,1 '-ferrocenylene spacer

    M Itazaki, O Kitami, M Tanabe, Y Nishihara, K Osakada

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   690 ( 17 )   3957 - 3962   2005年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    1,4-Bis(dimethylsilyl) benzene reacted with [Pt3H(PEt3)(3)(mu-PPh2)(3)] at room temperature to yield trinuclear Pt complex [Pt-3(SiMe2C6H4SiMe2H)(PEt3)(2) (mu-PPh2)(3)] (1a). Heating a solution containing an equimolar mixture of [Pt3H(PEt3)(3)mu PPh2)(3)] and 1a at 60 degrees C produced a hexanuclear Pt complex [(PEt3)(2)( mu-PPh2)(3)Pt-3(SiMe2C6H4SiMe2)Pt-3(PEt3)(2)(mu-PPh2)(3)] (2a). Complex 1a was characterized by X-ray crystallography and NMR spectroscopy, while the structure of 2a was determined by X-ray crystallography of single crystals containing 2a and [Pt3H2(PEt3)(2)(mu-PPh2)(4)] in 1:1 ratio. [Pt-3(SiMe(2)fcSiMe(2)H)(PEt3)(2)( mu-PPh2)(3)] (fc = Fe(eta(5)-C5H4)(2)) (1b) and [(PEt3)(2) (mu-PPh2)(3)Pt-3(SiMe(2)fcSiMe(2))Pt-3(PEt3)(2)(mu-PPh2)(3)] (2b) were obtained similarly from the reactions of 1,1 '-bis(dimethyisilyl)ferrocene with [Pt3H(PEt3)(3)(mu-PPh2)(3)] and characterized by NMR spectroscopy and elemental analyses. (c) 2005 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.jorganchem.2005.05.030

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  • Room-temperature palladium-catalyzed and copper(I)-mediated coupling reactions of acid chlorides with boronic acids under neutral conditions

    Y Nishihara, Y Inoue, M Fujisawa, K Takagi

    SYNLETT   ( 15 )   2309 - 2312   2005年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG KG  

    The palladium-catalyzed cross-coupling reactions of acid chlorides with arylboronic acids in the presence of copper(l) thiophene-2-carboxylate (CuTC) as an activator under strictly nonbasic and mild reaction conditions afford the unsymmetrical ketones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring is compatible.

    DOI: 10.1055/s-2005-872661

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  • Arylplatinum complexes with arylboronate ligands. Their preparation, structure, and relevance to transmetalation

    Pantcheva, I, Y Nishihara, K Osakada

    ORGANOMETALLICS   24 ( 16 )   3815 - 3817   2005年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The reactions of arylboronic acids with transPtPh(I)(PMe2Ph)(2) afford new arylboronato platinum complexes, trans-PtPh(OB(OH)Ar)(PMe2Ph)(2), and diarylplatinum complexes, trans-PtPh(Ar)(PMe2Ph)(2).

    DOI: 10.1021/om049050t

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  • Selective C-C bond activation of 2-aryl-1-methylenecyclopropanes promoted by Ir(I) and Rh(I) hydrido complexes. Mechanism of ring-opening isomerization of the strained molecules

    Y Nishihara, C Yoda, M Itazaki, K Osakada

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 8 )   1469 - 1480   2005年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    [IrH(CO)(PPh3)(3)] promotes ring opening of 2-phenyl-l-methylenecyclopropane at room temperature to produce the Ir complex with a chelating 2-phenyl-3-butenyl ligand, [Ir{eta(2)-CH2CH(Ph)CH=CH2-kappa C-1}(CO)(PPh3)(2)] (1). The reaction of excess 2-phenyl-l-methylenecyclopropane with [IrH(CO)(PPh3)(3)] at 50 degrees C yields [Ir{eta(2)-(o-C6H4)CH(Me)CH= CH2-kappa C-1)(CO)(PPh3)(2)] (2), accompanied by the formation of 1-phenyl-1,3-butadiene and 2-phenyl-1.3-butadiene. 2,2-Diphenyl-l-methylenecyclopropane reacts with [IrH(CO)(PPh3)(2)] to afford [Ir{eta(2)-CH2-CPh2CH=CH2-kappa C-1}(CO)-(PPh3)(2)] (3) at 50 degrees C and [Ir{eta(2)-(o-C6H4)CMe(Ph)CH=CH2-kappa C-1)(CO)(PPh3)(2)] (4) at 100 degrees C. Heating a solution of 3 at 100 degrees C also forms 4 quantitatively. X-ray crystallography of 3 reveals a penta-coordinated structure around the Ir center bonded to a chelating 2,2-diphenyl-3-butenyl ligand. The reactions of 2,2-diphenyl-l-methylenecyclopropane and of 2,2-di(4-fluorophenyt)-1-methylenecyclopropane with [RhH(CO)(PPh3)(3)] at room temperature yield [Rh{eta(2)- CH2CAr2CH=CH2-kappa C-1}(CO)(PPh3)(2)] (5a: Ar = Ph, 5b: Ar = C6H4-F-4). The reactions at 50 degrees C cause ring opening of the substrate and orthometalation of the phenyl group to afford [Rh{eta(2)-(o-C6H4)CMe(Ph)CH=CH2-kappa C-1}-(CO)(PPh3)(2)](6a) and [Rh{eta(2)-(o-C6H3-F-4)CMe(C6H4-F-4)CH=CH2-kappa C-1}(CO)(PPh3)(2)](6b), respectively. Formation of 1,1-diaryl-1,3-butadiene is observed during the reaction. Heating a solution of 5a at 50 degrees C produces 1,1-diphenyl-1,3-butadiene and an allylrhodium complex, 8, rather than 6a, although the reaction of excess 2,2-diphenyt-1-methylenecyclopropane with 5a at 50 degrees C affords 6a in 60 %. The mechanisms of the above reactions are discussed based on the products and reaction rates. Coordination of P(OMe)(3) to the Rh center of 5a causes insertion of the CO ligand into the Rh-C bond to afford [Rh{eta(2)-CO-CH2CPh2CH=CH2-kappa C-1}(P(OMe)(3))(3)] (7).

    DOI: 10.1246/bcsj.78.1469

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  • Dinuclear Pt(II) and Pd(I) complexes with bridging PPh2 ligands from the reaction of PPh2H with zero-valent complexes of these metals

    M Tanabe, M Itazaki, O Kitami, Y Nishihara, K Osakada

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 7 )   1288 - 1290   2005年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Reactions of PPh2H with [M(PCy3)(2)] (M = Pt, Pd) produce the dinuclear complexes with bridging PPh2 ligands of these metals, [{Pt(H)(PCy3)}(2)(mu-PPh2)(2)] and [{Pd-(PCy3)}(2)(mu-PPh2)(2)], respectively.

    DOI: 10.1246/bcsj.78.1288

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  • Palladium-catalyzed cyanoesterification of norbornenes with cyanoformates via the NC-Pd-COOR (R = Me and Et) intermediate

    Y Nishihara, Y Inoue, M Itazaki, K Takagi

    ORGANIC LETTERS   7 ( 13 )   2639 - 2641   2005年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Palladium-catalyzed cyanoesterification of norbornenes proceeds stereoselectively via NC-Pd-COOR (R = Me and Et) complexes as intermediates.

    DOI: 10.1021/ol050749k

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  • Diarylpalladium complexes with a cis structure. Formation via transmetalation of arylboronic acids with an aryliodopalladium complex and intramolecular coupling of the aryl ligands, affording unsymmetrical biaryls

    K Osakada, H Onodera, Y Nishihara

    ORGANOMETALLICS   24 ( 2 )   190 - 192   2005年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    (2,4,6-Trifluorophenyl)- and (2,6-difluorophenyl)boronic acids react with PdI(C6H4O4-Me)(tmen) (tmen = N,N,N',N'-tetramethylethylenediamine) in the presence of Ag2O to produce cis-diarylpalladium complexes with a tmen ligand via intermolecular transfer of the fluorophenyl group from B to Pd. The isolated complexes undergo coupling of the two aryl ligands upon heating the solution to 45-60 degreesC to afford unsymmetrical biaryls.

    DOI: 10.1021/om049217i

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  • C-C and C-H bond activation of dialkylmethylenecyclopropane promoted by rhodium and iridium complexes. Preparation and structures of M(eta(1):eta(2)-CH2CR2CH=CH2)(CO)(PPh3)(2) and trans-M(CH=CHCMeR2)(CO)(PPh3)(2) (M = Rh, Ir, R = CH2CH2Ph)

    M Itazaki, C Yoda, Y Nishihara, K Osakada

    ORGANOMETALLICS   23 ( 23 )   5402 - 5409   2004年11月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    2,2-Bis(2-phenylethyl)-1-methylenecyclopropane reacts with RhH(CO)(PPh3)(3) at room temperature and with IrH(CO)(PPh3)(3) at 70 degreesC to form the 3-butenyl complexes of these metals, M{eta(1):eta(2)-CH2C(CH2CH2Ph)(2)CH=CH2}(CO)(PPh3)(2) (1, M = Rh; 2, M = Ir). Heating 1 at 55 degreesC liberates 1,1-bis(2-phenylethyl)-1,3-butadiene, while the thermal reaction of 2 at 110 degreesC forms a mixture of 3-methyl-3-vinyl-1,5-diphenyl-1-pentene (48% NMR yield) and 3-methyl-3-vinyl-1,5-diphenylpentane (15% NMR yield). The reactions of excess amounts of 2,2-bis(2-phenylethyl)-1-methylenecyclopropane with RhH(CO)(PPh3)(3) at 55 degreesC and with IrH(CO)(PPh3)(3) at 115 degreesC afford the alkenyl complexes trans-Rh{(Z)-CH=CHC(CH2CH2Ph)(2)CH3}-(CO)(PPh3)(2) (3) and trans-Ir{(E)-CH=CHC(CH2CH2Ph)(2)CH3}(CO)(PPh3)(2) (4), respectively. The reaction mechanisms are discussed on the basis of the results of the reactions under different conditions. HCequivalent toCC(CH2CH2Ph)(2)CH3 reacts with MH(CO)(PPh3)(3) (M = Rh, Ir) to afford the alkynyl complexes trans-M{Cequivalent toCC(CH2CH2Ph)(2)CH3}(CO)(PPh3)(2) (5, M = Rh; 6, M = Ir) via oxidative addition of the C(alkyne)-H bond to the metal center and subsequent elimination of H-2.

    DOI: 10.1021/om049632a

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  • Cationic Rh complexes with novel spiro tetraarylpentaborate anions prepared from arylboronic acids and aryloxorhodium complexes

    Y Nishihara, K Nara, Y Nishide, K Osakada

    DALTON TRANSACTIONS   ( 9 )   1366 - 1375   2004年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Ar-B(OH)(2) (1a: Ar = C6H4OMe-4, 1b: Ar = C6H3Me2-2,6) react immediately with Rh(OC6H4Me-4)(PMe3)(3) (2) in 5 : 1 molar ratio at room temperature to generate [Rh(PMe3)(4)](+)[B5O6Ar4](-) (3a: Ar C6H4OMe-4, 3b: Ar = C6H3Me2- 2,6). p-Cresol (92%/Rh), anisole (80%/Rh) and H2O (364%/Rh) are formed from 1a and 2. The reaction of 1a with 2 for 24 h produces [Rh(PMe3)(4)](+)[B5O6(OH)(4)](-) (4) as a yellow solid. This is attributed to hydrolytic dearylation of once formed 3a because the direct reaction of 3a with excess H2O forms 4. An equimolar reaction of 2 with phenylboroxine (PhBO)(3) causes transfer of the 4-methylphenoxo ligand from rhodium to boron to produce [Rh(PMe3)(4)](+) [B3O3Ph3(OC6H4Me-4)](-) (5). Arylboronic acids 1a and 1b react with Rh(OC6H4Me-4)(PR3)(3) (6: R = Et, 8: R = Ph) and with Rh(OC6Me-4)(cod)(PR3) (11: R = Pr-i, 12: R = Ph) to form [Rh(PR3)(4)](+)[B5O6Ar4](-) (7a: R = Et, Ar = C6H4OMe-4, 7b: R = Et, Ar = C6H3Me2-2,6, 9a: R = Ph, Ar = C6H3Me2-2,6) and [Rh(cod)(PR3)(L)](+)[B5O6Ar4](-) (13b: R = Pr-i, L = acetone, Ar = C6H3Me2-2,6,14a: R = Ph L = PPh3, Ar = C6H4OMe-4, 14b: R = Ph, L = PPh3, Ar - C6H3Me2-2,6), respectively. Hydrolysis of 14a yields [Rh(cod)(PPh3)(2)](+)[B5O6(OH)(4)](-) (15) quantitatively.

    DOI: 10.1039/b315902g

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  • Stereodivergent syntheses of (Z)- and (E)-alkenylsilanes via hydrosilylation of terminal alkynes catalyzed by rhodium(I) iodide complexes and application to silicon-containing polymer syntheses

    A Mori, E Takahisa, Y Yamamura, T Kato, AP Mudalige, H Kajiro, K Hirabayashi, Y Nishihara, T Hiyama

    ORGANOMETALLICS   23 ( 8 )   1755 - 1765   2004年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    RhI(PPh3)(3) or [RhI(cod)](2) (cod = 1,5-cyclooctadiene) as a catalyst delivers both (Z)- and (E)-alkenylsilanes in the stereodivergent hydrosilylation of terminal alkynes with heteroatom-substituted organosilane reagents. Treatment of the rhodium catalyst and the silane reagent followed by addition of terminal alkyne at room temperature leads to (Z)-silanes, while addition of the silane and the alkyne to the rhodium catalyst in one portion and heating at 60 degreesC affords (E)-silanes highly selectively. The obtained (E)- and (Z)-alkenylsilanes bearing heteroatom substituents on the silicon atom are subjected to the palladium-catalyzed cross-coupling reaction with aryl halides to form a carbon-carbon bond with retention of stereochemistry. The stereodivergent hydrosilylations are applied to the polyaddition with bifunctional alkynes (1,3- and 1,4-diethynylbenzene) and silanes (1,3- or 1,4-bis(dimethyl-silyl)benzene), giving silicon-containing polymers, poly(aryleneethenylenesilylene)s, in highly stereocontrolled manners. A fluorine-containing silicon reagent bearing a 3,3,3-trifluoropropyl group is also subjected to the polymerization, in which [RhI(cod)12 is found to be an efficient catalyst. Measurement of UV-vis absorption/emission spectra and several. thermal analyses of the polymers are also conducted.

    DOI: 10.1021/om049922r

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  • Syntheses of Dinuclear and Trinuclear Hydridoplatinum Complexes with Bridging Phosphido Ligands [Pt2H2(m-PR2)2(PEt3)2] (R = tBu, Ph) and [Pt3H2(m-PPh2)4(PEt3)2]. Characterization of the Triangular Intermediate [Pt3H(m-PPh2)3(PEt3)3] and Its Chemical Pr・・・

    M. Itazaki, Y. Nishihara, K. Osakada

    Organometallics   23 ( 7 )   1610 - 1621   2004年3月

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    記述言語:英語  

    Syntheses of Dinuclear and Trinuclear Hydridoplatinum Complexes with Bridging Phosphido Ligands [Pt2H2(m-PR2)2(PEt3)2] (R = tBu, Ph) and [Pt3H2(m-PPh2)4(PEt3)2]. Characterization of the Triangular Intermediate [Pt3H(m-PPh2)3(PEt3)3] and Its Chemical Properties

    DOI: 10.1021/om034131v

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  • Synthesis and structural characterization of the first unsymmetrical diarylpalladium complex trans-Pd(C6F5)(2,4,6-C6F3H2)(PEt3)(2), derived from transmetallation between 2,4,6-trifluorophenylboronic acid and trans-Pd(C6F5)I(PEt3)(2)

    Y Nishihara, H Onodera, K Osakada

    CHEMICAL COMMUNICATIONS   ( 2 )   192 - 193   2004年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    The reactions of 2,4,6-trifluorophenylboronic acid with aryl(iodo)palladium(II) complexes, trans-Pd(C6F5)I(PR3)(2)(PR3 = PEt3, PMe2Ph, PMePh2) in the presence of Ag2O afforded transPd(C6F5)(2,4,6-C6F3H2)(PR3)(2) which are stabilized by fluorine atoms in the ortho positions.

    DOI: 10.1039/b308741g

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  • New stable complexes of Au(III) with biuret: X-ray structure of cis-[Au(Biu)Br-2]PPh4 and Ab initio investigation of cis-[Au(Biu)X-2](-)

    N Mintcheva, M Mitewa, Enchev, V, Y Nishihara

    JOURNAL OF COORDINATION CHEMISTRY   56 ( 4 )   299 - 305   2003年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS LTD  

    Two anionic complexes of Au(III) with the bioligand biuret, cis-[Au(Biu)X-2](-) (BiuH(2)=biuret, X=Cl, Br), have been synthesized and characterized. The molecular structure of cis-[Au(Biu)Br-2]PPh4 has been determined by X-ray diffraction analysis. The complex anion has square-planar geometry with one deprotonated biuret dianion coordinated bidentately to the metal center via the terminal amino nitrogen atoms and two bromide ions in cis positions. There are no significant intermolecular Au-Au interactions in the solid state. Ab initio calculations of the geometric structure at different computational levels for biuret and both anionic complexes as well an IR study of the structures obtained are performed.

    DOI: 10.1080/0095897031000069049

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  • Platinum complex-catalyzed hydrosilylation and isomerization of methylenecyclopropane derivatives. Effect of structures of the substrate and catalyst

    M Itazaki, Y Nishihara, K Osakada

    JOURNAL OF ORGANIC CHEMISTRY   67 ( 20 )   6889 - 6895   2002年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    PtI2(PPh3)(2) catalyzes hydrosilylation of 2,2-diphenyl-1-methylenecyclopropane with HSiEt3, HSiPh3, HSiEt2Ph, HSiPhCl2, and HSiCl3 under solvent-free conditions at 140 degreesC to produce the silyl compounds with a (2,2-diphenyleyclopropyl)methyl substituent in moderate to high yields without ring-opening of the substrate. PtI2(PPh3)(2) is converted by the reaction into PtH(I)(PPh3)(2), which also catalyzes the hydrosilylation of the methylenecyclopropanes. The reaction of 2-phenyl-1-methylenecyclopropane, 2-methyl-2-phenyl-1-methylenecyclopropane, 2,2-diphenethyl-1-methyl-enecyclopropane, and alkylidenecyclopropanes with HSiEt3 catalyzed by PtI2(PPh3)(2) causes addition of hydrosilane to the substrate accompanied by ring-opening. 2,2-Diphenyl-1-methylenecyclopropane undergoes ring-opening isomerization in the presence of HSi(OEt)Me-2 and Pt(PEt3)(3) catalyst to give 1,1-diphenyl-1,3-butadiene. The pathways for the hydrosilylation and the isomerization are discussed.

    DOI: 10.1021/jo020293+

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  • Tetraarylpentaborates, [B5O6Ar4](-) (Ar = C6H4OMe-4, C6H3Me2-2,6): Their formation from the reaction of arylboronic acids with an aryloxorhodium complex, structure, and chemical properties

    Y Nishihara, K Nara, K Osakada

    INORGANIC CHEMISTRY   41 ( 16 )   4090 - 4092   2002年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The reactions of (4-methoxyphenyl)boronic acid (1a) and of (2,6-dimethylphenyl)boronic acid (1 b) with (PMe3)(3)Rh-(OC6H4Me-4) (2) in a 5:1 molar ratio result in the formation of cationic rhodium complexes with new tetraarylpentaborates [Rh(PMe3)(4)](+)[B5O6Ar4](3a, Ar = C6H4OMe-4; 3b, Ar = C6H3Me2-2,6). The characterization of 3a is as follows: orthorhombic space group P2(1)2(1)2(1), a = 14.7600(5) Angstrom, b =17.1675(5) Angstrom, c = 19.8654(5) Angstrom; V = 5033.7(3) Angstrom(3); Z = 4. The characterization of 3b is as follows: orthorhombic space group Pnma, a = 23.704(6) Angstrom, b = 17.254(8) Angstrom, c = 13.304(2) Angstrom; V = 5441(2) Angstrom(3); Z = 4. An intermediate complex, [Rh(PMe3)(4)](+)[Ph3B3O3(OC6H4Me-4)](-) (4), was isolated from the reaction of phenylboroxine, (PhBO)(3), with 2. The tetraarylpentaborates smoothly undergo hydrolysis to give [Rh(PMe3)(4)](+)[B5O6(OH)(4)](-) (5).

    DOI: 10.1021/ic015630w

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  • Platinum complex-catalyzed hydrosilylation of 2,2-diaryl-1-methylenecyclopropane affording (silylmethyl)cyclopropane

    Y Nishihara, M Itazaki, K Osakada

    TETRAHEDRON LETTERS   43 ( 11 )   2059 - 2061   2002年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    PtI2(PPh3)(2)-catalyzed hydrosilylation of 2.2-diphenyl-1-methylenecyclopropane with HSiEt3 forms (2,2-diphenylcyclopropyl)methyl(triethyl)silane in 87% yield as a sole product. This highly selective addition of Si-H bond converts 2,2-diaryl-1-methylenecyclopropane into its silylated derivative without ring-opening. (C) 2002 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(02)00165-X

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  • Structure and properties of halogeno(hydrido) (triorganosilyl)rhodium(III) complexes, RhX(H) ((SiRnR3-n2)-R-1)(PPh3)(2) (X = Cl, I; R-1 = OSiMe3, OEt, R-2 = Me). Influence of the alkoxy groups and halo ligand on stability and reactivity of the complexes

    Y Nishihara, M Takemura, K Osakada

    ORGANOMETALLICS   21 ( 5 )   825 - 831   2002年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Silylrhodium(III) complexes RhX(H)((SiRnR3-n2)-R-1)(PPh3)(2) (1: X = I, R-1 = OSiMe3, R-2 = Me, n = 1; 2: X= I, R-1 = OEt,n = 3; 3: X = I, R-1 = OEt, R-2 = Me, n = 2; 4: X=I, R-1 = OEt, R-2 = Me, n = 1; 5: X= Cl, R-1 = OSiMe3, R-2 = Me, n = 1; 6: X = Cl, R-1 = OEt, n = 3; 7: X = Cl, RI = OEt, R2 = Me, n = 2; 8: X = Cl, R-1 = OEt, R-2 = Me, n = 1) were prepared by oxidative addition of (HSiRnR3-n2)-R-1 to RhX(PPh3)(3) and characterized by means of NMR (H-1, C-13{H-1}, P-31{H-1}, and Si-29{H-1}) and IR spectroscopy as well as elemental analyses. X-ray crystallography of 1, 2, and 6 showed a distorted square-pyramidal coordination around the Rh center that is bonded to the silyl ligand at the apical position and to halo and hydrido ligands in trans positions in the basal plane. The Rh-Si bonds in 2 and 6 are the shortest among Rh-Si bonds of the silylrhodium complexes reported to date. Si-29{H-1} NMR spectra of 1-8 show that the J(RhSi) value increases with an increase in the number of alkoxy substituents on the Si atom. Complex 2 reacted with HSiMe2(OSiMe3), HSi(OEt)(2)Me, and HSi(OEt)Me-2, respectively, to cause exchange of the silyl group between the Rh complex and the organosilane, forming an equilibrium mixture. Complexes 5-8 undergo thermally induced coupling of their chloro and triorganosilyl ligands at 60 degreesC to liberate the respective chloro(triorgano)silane. The reaction obeys first-order kinetics in the Rh complex with the observed rate constants in the order 5 congruent to 8 > 7 > 6. The OEt groups at the Si retard the coupling of chloro and triorganosilyl ligands significantly. Formation of ISiMe2(OEt)(2) from 4 takes place at a slightly slower rate than the reaction of 6, while complexes 2 and 3 do not undergo coupling of their iodo and silyl ligands at 60 degreesC.

    DOI: 10.1021/om010862o

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  • Isomerization of (Z)-alkenylsilanes to (E)-isomers with hydrosilane and RhI(PPh3)(3)

    A Mori, E Takahisa, Y Nishihara, T Hiyama

    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE   79 ( 11 )   1522 - 1524   2001年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:NATL RESEARCH COUNCIL CANADA  

    Isomerization of (E)-2-phenylethenylsilanes to the (Z)-isomers is found to easily take place at 60 degreesC within 1 h using 20-100 mol% of a hydrosilane and 0.1 mol% of RhI(PPh3)(3) and is understood in terms of insertion of alkenylsilanes to hydridorhodium followed by beta -hydride elimination.

    DOI: 10.1139/cjc-79-11-1522

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  • Homo-coupling polycondensation of bis(alkynylsilane)s mediated by copper(I) chloride: A new synthesis of poly(arylenebutadiynylene)s

    Y Nishihara, T Kato, J Ando, A Mori, T Hiyama

    CHEMISTRY LETTERS   ( 10 )   950 - 951   2001年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Homo-coupling polycondensation of aromatic compounds bearing two (trimethylsilyl)ethynyl groups mediated by copper(I) chloride in DMF gives conjugated poly(arylenebutadiynylene)s in up to 94% yield with molecular weight of 4000-8900 (M-w/M-n = 1.78-2.09).

    DOI: 10.1246/cl.2001.950

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  • Preparation and reactions of monocyclic bis(cyclopentadienyl)titanacyclopentenes and -pentadienes

    K Sato, Y Nishihara, SQ Huo, ZF Xi, T Takahashi

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   633 ( 1-2 )   18 - 26   2001年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    A combination of CP2TiCl2-2EtMgBr was found to be very effective for the formation of monocyclic titanacyclopentenes in excellent yields. On the other hand, a combination of Cp2TiCl2-2n-BuLi was used for intermolecular coupling of two alkynes to form titanacyclopentadienes in good to excellent yields. A reaction temperature range from -10 to -30 degreesC was critical for the success of the combinations. Reactions of these in situ-prepared titanacycles show interesting similarities to or differences from their zirconacycle analogs. (C) 2001 Published by Elsevier Science BN.

    DOI: 10.1016/S0022-328X(01)01072-5

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  • Reactions of HOSiMe2Ar with PtPPh3 complexes leading to Si-C bond activation or formation of a siloxoplatinum complex

    N Mintcheva, Y Nishihara, A Mori, K Osakada

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   629 ( 1-2 )   61 - 67   2001年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    PtI2(PPh3)(2) reacts with HOSiMe2(C6H4CF3-4) at 60 degreesC in the presence of AgBF4 to give a mixture of trans-PtI(C6H4CF3-4)(PPh3)(2) (1) and [Pt-2(mu -I)(2)(PPh3)(4)](BF4)(2) (2). Each of the complexes is isolated and characterized by X-ray crystallography and/or NMR spectroscopy. The P-31{H-1}-NMR study of the reaction of AgBF4 with PtI2(PPh3)(2) in acetone-d(6) revealed the formation of trans-[PtI(PPh3)(2)(acetone)]BF4 (3) although isolation of the cationic complex was not feasible due to its facile conversion to 2. Addition of HOSiMe2(C6H4CF3-4) and Ag2O to a toluene Solution of trans-PtI(Ph)(PPh3)(2) causes replacement of the iodo ligand with the siloxo group to afford trans-[Pt(Ph) {OSiMe2(C6H4CF3-4)} (PPh3)(4)] (4). Crystallographic results of 4 show the coordination of the phenyl, siloxo, and PPh3 ligands to the square-planar Pt center with a large Pt-O-Si angle. Complex 4 does not decompose below 60 degreesC in a toluene solution, but reacts with CH2Cl2 and CHCl3 at room temperature to form trans-Pt-Cl(Ph)(PPh3)(2) (5). (C) 2001 Elsevier Science B.V. All rights reserved.

    DOI: 10.1016/S0022-328X(01)00796-3

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  • Hydrido-Rhodium(I) and -Iridium(I) complex promoted ring-opening isomerization of unsymmetrically substituted methylenecyclopropanes into 1,3-dienes. Structures of intermediates and reaction pathways

    Y Nishihara, C Yoda, K Osakada

    ORGANOMETALLICS   20 ( 11 )   2124 - 2126   2001年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    2-Phenyl-1-methylenecyclopropane and 2,2-diphenyl-1-methylenecyclopropane react with MH(CO)(PPh3)(3) (M = Rh, Ir) to produce 1,3-dienes or the intermediate Rh and Ir complexes having a 3-butenyl ligand, depending on the conditions. The structures and chemical properties of the obtained complexes suggest plausible pathways for the ring-opening isomerization of the methylenecyclopropanes to the corresponding dienes.

    DOI: 10.1021/om010081n

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  • Palladium-catalyzed cross-coupling polycondensation of bisalkynes with dihaloarenes activated by tetrabutylammonium hydroxide or silver(I) oxide

    A Mori, T Kondo, T Kato, Y Nishihara

    CHEMISTRY LETTERS   ( 4 )   286 - 287   2001年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The palladium(O)-catalyzed polycondensation of bis-trimethylsilylethynylated compounds with diiodoarenes to give the polymers bearing arylene-ethynylene moieties is carried out by the use of silver(I) oxide as an activator. Polycondensation of bifunctional terminal alkynes and aryl halides is also accomplished by the palladium-catalyzed cross coupling in the presence of tetrabutylammonium hydroxide (TBAOH), tetrabutylammonium fluoride (TBAF), or silver(I) oxide.

    DOI: 10.1246/cl.2001.286

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  • Si-C bond activation of ArMe2SiOH promoted by a bromoplatinum(II) complex and Ag2O. Aryl group transfer from silicon to platinum

    N Mintcheva, Y Nishihara, M Tanabe, K Hirabayashi, A Mori, K Osakada

    ORGANOMETALLICS   20 ( 6 )   1243 - 1246   2001年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [PtBr(PEt3)(3)]BF4 (1) reacts with art excess of dimetliyl{4-(trifluoromethyl)phenyl}silanol in the presence of Ag2O and 4 Angstrom molecular sieves at 60 OC to afford trans-Pt(C6H4CF3-4)(2)(PEt3)(2) (2) The reaction without molecular sieves and that with addition of a smalE amount of water give a mixture of 2 and [Pt-2(mu -OH)(2)-(PEt3)(4)](BF4)(2). The organic products of the reaction are composed of ArSiMe2-O-(SiMe2-O)(n)-SiMe2Ar (Ar = C6H4 CF3-4, n = 0, 1, 2) a nd cyclooligodimethylsiloxanes in lesser amounts. The obtained complexes were characterized by NMR spectroscopy and X-ray crystallography.

    DOI: 10.1021/om010006c

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  • Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu

    Y Nishihara, M Takemura, A Mori, K Osakada

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   620 ( 1-2 )   282 - 286   2001年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100 degreesC in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species[Cu2Cl(C drop CPh)(n)] (1) in 56-63% yields. Heating 1 at 80 degreesC under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands. (C) 2001 Elsevier Science B.V. All rights reserved.

    DOI: 10.1016/S0022-328X(00)00794-4

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  • Non-Sonogashira-type palladium-catalyzed coupling reactions of terminal alkynes assisted by silver(I) oxide or tetrabutylammonium fluoride

    A Mori, J Kawashima, T Shimada, M Suguro, K Hirabayashi, Y Nishihara

    ORGANIC LETTERS   2 ( 19 )   2935 - 2937   2000年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    Palladium-catalyzed reaction of aryl and alkenyl halides with terminal alkynes in the presence of silver(I) oxide as an activator furnishes various arylated or alkenylated alkynes in good to excellent yields, The similar coupling reaction is also found to proceed using tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide (TBAOH) as an activator.

    DOI: 10.1021/ol0061586

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  • Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

    E Hirabayashi, A Mori, J Kawashima, M Suguro, Y Nishihara, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 17 )   5342 - 5349   2000年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling products in excellent yields within shorter reaction periods (5-12 h). The measurement of the X-ras diffraction (XRD) pattern of the silver residue after the reaction revealed that silver(I) oxide was converted to silver(I) iodide.

    DOI: 10.1021/jo000679p

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  • Novel carbon-carbon bond formation through Mizoroki-Heck type reaction of silanols and organotin compounds

    K Hirabayashi, J Ando, J Kawashima, Y Nishihara, A Mori, T Hiyama

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 6 )   1409 - 1417   2000年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The reaction of dimethyl(phenyl)silanol with butyl acrylate in the presence of a stoichiometric amount of Pd(OAc)(2) or by a combined use of 0.1 molar amount of Pd(OAc)(2) and Cu(OAc)(2)/LiOAc (molar ratio 3/2) gave butyl cinnamate in 76% or 57% yield, respectively. The similar reaction with tributyl(phenyl)tin also proceeded in 77% yield. The organotin compound was shown to react faster than the silanol, although the tin reagent sometimes induced undesirable homo-coupling, while the reaction with silanol did not give such by-product.

    DOI: 10.1246/bcsj.73.1409

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  • A novel cross-coupling polycondensation of alkynylsilanes with aryl triflates catalyzed by CuCl/Pd(PPh3)(4)

    Y Nishihara, J Ando, T Kato, A Mori, T Hiyama

    MACROMOLECULES   33 ( 8 )   2779 - 2781   2000年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ma9908301

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  • Home-coupling reactions of alkenyl- and arylfluorosilanes mediated by a copper(I) salt

    Y Nishihara, K Ikegashira, F Toriyama, A Mori, T Hiyama

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 4 )   985 - 990   2000年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Home-coupling reactions of an alkenyl- or arylsilane readily occur with a copper(I) salt in an aprotic polar solvent such as N, N-dimethylformamide or dimethyl sulfoxide under an aerobic condition to give the corresponding conjugated dienes or biaryls, respectively. Optimization of a copper salt and a solvent for the home-coupling reaction is discussed. The formation of the organocopper intermediates is evidenced by trapping experiments with iodine and by a conjugate addition to methyl vinyl ketone.

    DOI: 10.1246/bcsj.73.985

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  • Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes

    Y Nishihara, K Ikegashira, K Hirabayashi, J Ando, A Mori, T Hiyama

    JOURNAL OF ORGANIC CHEMISTRY   65 ( 6 )   1780 - 1787   2000年3月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 OC under an aerobic conditions smoothly undergoes home-coupling to give the corresponding symmetrical 1,3-butadiynes in 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found to couple with aryl triflates and chlorides in the presence of Cu(I)/Pd(0) (10 mol %/5 or 10 mol %) cocatalyst system to give the corresponding diarylethynes in 49-99% yields. The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-coupling reactions using two different aryl triflates. The reactions of (arylethynyl)trimethylsilanes with aryl(chloro)ethynes in the presence of 10 mol % of CuCl also yield the corresponding unsymmetrical 1,3-butadiynes in 43-97% yields.

    DOI: 10.1021/jo991686k

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  • Substituent effect of 3,3,3-trifluoropropyl group on organic silanols. Palladium-mediated Mizoroki-Heck type and cross-coupling reactions

    K Hirabayashi, T Kondo, F Toriyama, Y Nishihara, A Mori

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 3 )   749 - 750   2000年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The Mizoroki-Heck type reaction of methyl(phenyl)(3,3,3-trifluoropropyl)silanol (1a) with ethyl acrylate in the presence of Pd(OAc)(2) (10 mol%) and Cu(OAc)(2)/LiOAc gave ethyl cinnamate in 70% yield. The palladium-catalyzed cross-coupling of la with 4-iodomethoxybenzene in the presence of Ag2O also afforded 4-methoxybiphenyl in 51% yield.

    DOI: 10.1246/bcsj.73.749

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  • Stereodivergent hydrosilylation of 1-alkynes catalyzed by RhI(PPh3)(3) leading to (E)- and (Z)-alkenylsilanes and the application to polymer synthesis

    A Mori, E Takahisa, H Kajiro, Y Nishihara, T Hiyama

    POLYHEDRON   19 ( 5 )   567 - 568   2000年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Hydrosilylation of 1-alkynes catalyzed by RhI(PPh3)(3) gives (E)- and (Z)-alkenylsilanes in a stereodivergent manner by switching the reaction conditions and the order of the addition of the reagents. The reaction is also applied to the synthesis of silicon-containing polymers with (E) and (Z) main-chain structures via polyaddition. (C) 2000 Elsevier Science Ltd All rights reserved.

    DOI: 10.1016/S0277-5387(99)00409-X

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  • Regio- and stereocontrolled hydrosilylation polyaddition catalyzed by RhI(PPh3)(3). Syntheses of polymers containing (E)- or (Z)-alkenylsilane moieties

    A Mori, E Takahisa, H Kajiro, Y Nishihara, T Hiyama

    MACROMOLECULES   33 ( 4 )   1115 - 1116   2000年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ma9913360

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  • Preparation and characterization of bis(cyclopentadienyl)zirconium(II) complexes with a tethered olefin-phosphine ligand

    A Yamazaki, Y Nishihara, K Nakajima, R Hara, T Takahashi

    ORGANOMETALLICS   18 ( 16 )   3105 - 3108   1999年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Unprecedented zirconium(II) complexes bearing tethered olefin-phosphine ligands were synthesized and characterized. The molecular structures of the newly synthesized complexes (eta(5)-1,2-Me2C5H3)(2)Zr(CH2=CHCH2CH2PPh2) (1c) and Cp2Zr(CH2=CHCH2CH2CH2PPh2) (2a) were determined by single-crystal X-ray diffraction methods. The stability and reactivity of the series of complexes Cp2Zr{CH2=CH(CH2)(n)PR2} (n = 2, 3; R = Et, Ph) were examined. The complex 2a showed simultaneously both sufficient stability and high reactivity.

    DOI: 10.1021/om990103u

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  • Synthesis and optical resolution of novel chiral silanols

    A Mori, F Toriyama, H Kajiro, K Hirabayashi, Y Nishihara, T Hiyama

    CHEMISTRY LETTERS   ( 7 )   549 - 550   1999年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Silanols bearing an asymmetric center on silicon, methyl(2-phenylethenyl) (3,3,3-trifluoropropyl)silanol and methyl(phenyl)(vinyl)silanol are synthesized by alkylative cleavages of cyclic siloxanes with an organolithium. Optical resolution of their enantiomers is performed by HPLC with a chiral stationary phase column. Optical characters of thus separated enantiomers are also examined.

    DOI: 10.1246/cl.1999.549

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  • A new transformation of silanols. Palladium-catalyzed cross-coupling with organic halides in the presence of silver(I) oxide

    K Hirabayashi, J Kawashima, Y Nishihara, A Mori, T Hiyama

    ORGANIC LETTERS   1 ( 2 )   299 - 301   1999年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    [GRAPHICS]
    The reactions of aryl- and alkenylsilanols with organic halides are found to proceed in a catalyst system of 5 mol % of Pd(PPh3)(4) and Ag2O (1 equiv) to give the corresponding coupling products in up to 84% yield.

    DOI: 10.1021/ol990614c

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  • A unique chelating effect of Sc(OTf)(3) to organofluorine compounds

    H Kajiro, A Mori, Y Nishihara, T Hiyama

    CHEMISTRY LETTERS   ( 6 )   459 - 460   1999年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    The scandium trifluoromethanesulfonate-catalyzed cleavage of acetate bearing two or three fluorine atoms at a position beta to an acetoxy group proceeds exceptionally rapidly. The high efficiency of the hydrolysis is caused by a chelating effect of scandium with the fluorine atoms and an acetate moiety.

    DOI: 10.1246/cl.1999.459

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  • Conjugate reduction of alpha,beta-unsaturated ketones with hydrosilane mediated by copper(I) salt

    A Mori, A Fujita, H Kajiro, Y Nishihara, T Hiyama

    TETRAHEDRON   55 ( 15 )   4573 - 4582   1999年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Reduction of several alpha,beta-unsaturated ketones with dimethylphenylsilane and 10-100 mol% of CuF(PPh3)(3). 2EtOH or CuCl/PPh3/Bu4NF proceeds in a 1,4-selective manner to give the corresponding saturated ketones in up to >99% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4020(99)00141-6

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  • A coupling reaction of aryltributyltin with olefins mediated by palladium(II) acetate

    K Hirabayashi, J Ando, Y Nishihara, A Mori, T Hiyama

    SYNLETT   ( 1 )   99 - 101   1999年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:GEORG THIEME VERLAG  

    Phenytributyltin is found to react with butyl acrylate in the presence of Pd(OAc)(2) (10 mol%), Cu(OAc)(2) (3 mel), and LiO-Ac (2 mel) in DMF to afford butyl 3-phenylpropenoate in 77% yield. Methyl vinyl ketone, acrolein, acrylonitrile, and styrene are also applicable to this reaction as a substrate.

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  • Copper(I)-catalyzed cross-coupling reaction of alkynylsilanes with 1-chloroalkynes 査読

    Nishihara Y, Ikegashira K, Mori A, Hiyama T

    Tetrahedron Letters   39 ( 23 )   4075 - 4078   1998年

  • RhCl(PPh3)(3)/NaI catalyst system for hydrosilylation of 1-alkynes: Stereodivergent syntheses of E- and Z-alkenylsilanes with heteroatom substituents on silicon 査読

    Mori A, Takahisa E, Kajiro H, Hirabayashi K, Nishihara Y, Hiyama T

    Chemistry Letters   ( 5 )   443 - 444   1998年

  • A novel C-C bond forming reaction of aryl- and alkenylsilanols. A halogen-free Mizoroki-Heck type reaction 査読

    Hirabayashi K, Nishihara Y, Mori A, Hiyama T

    Tetrahedron Letters   39 ( 43 )   7893 - 7896   1998年

  • A facile preparation and cyclopropanation of 1-alkenylsilanols 査読

    Hirabayashi K, Takahisa E, Nishihara Y, Mori A, Hiyama T

    Bulletin of the Chemical Society of Japan   71 ( 10 )   2409 - 2417   1998年

  • Preparation and reactions of Cp2HfRCl, Cp2HfRR′ and hafnacyclopent-2-enes 査読

    Yasushi Nishihara, Toyohisa Ishida, Shouquan Huo, Tamotsu Takahashi

    Journal of Organometallic Chemistry   547 ( 2 )   209 - 216   1997年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Elsevier  

    Reaction of Cp2HfCl2 with R3Al (R = Et, n-Pr, or n-Bu) in hexane selectively produced monoalkylhafnocene complexes, Cp2HfRCl (1), in high yields. Cp2HfMeCl (1a) was prepared by the reaction of oxo-bridged hafnocene complex (Cp2HfCl)2(μ-O) with Me3Al. The treatment of 1 with alkylating reagents such as R′Li or EtMgBr afforded unsymmetrical dialkylhafnocene complexes Cp2HfRR′ (3) in good to excellent yields. The kinetic study of thermolysis of Cp2HfEtR (R = Me, Et, n-Bu, sec-Bu, t-Bu or Ph) suggested that decomposition of Cp2HfEt(sec-Bu) was much faster than the others. Cp2Hf(sec-Bu)2 (2e) can be used as a good precursor of Cp2Hf(II) species. Hafnacyclopent-2-enes (4) were prepared in good yields by the reaction of Cp2HfEt2 (2b) with alkynes. © 1997 Elsevier Science S.A.

    DOI: 10.1016/S0022-328X(97)00375-6

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  • Highly regio- and diastereo-selective carbon-carbon bond formation reaction of unsymmetrical zirconacyclopentanes using copper salt 査読

    T Takahashi, Y Nishihara, R Hara, SQ Huo, M Kotora

    CHEMICAL COMMUNICATIONS   ( 17 )   1599 - 1600   1997年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Reaction of unsymmetrical zirconacyclopentanes with allyl chloride or benzoyl chloride in the presence of copper chloride gave allylated or benzoylated products with high regio- and diastereo-selectivities.

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  • Convenient preparative method of alpha,beta-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO 査読

    T Takahashi, ZF Xi, Y Nishihara, SQ Huo, K Kasai, K Aoyagi, Denisov, V, E Negishi

    TETRAHEDRON   53 ( 27 )   9123 - 9134   1997年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I-2 gave alpha,beta-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, alpha-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, alpha-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynytbenzene afforded alpha alpha'-bridged cyclopentenone compounds in good yields. (C) 1997 Elsevier Science Ltd.

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  • Coupling reaction of alkenylzirconocenes with aryl or alkenyl iodides in the presence of CuCl/Pd(PPh(3))(4) 査読

    R Hara, Y Nishihara, PD Landre, T Takahashi

    TETRAHEDRON LETTERS   38 ( 3 )   447 - 450   1997年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Trisubstituted alkenylalkoxyzirconocenes which have been prepared from carbozirconation reactions of internal alkynes via zirconacyclopentenes reacted with aryl or alkenyl iodides in the presence of CuCl and a catalytic amount of Pd(PPh(3))(4) to give coupling products. Copyright (C) 1996 Elsevier Science Ltd

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  • Zirconocene catalyzed dehalogenation of aromatic halides by alkylmagnesium reagents 査読

    R Hara, WH Sun, Y Nishihara, T Takahashi

    CHEMISTRY LETTERS   ( 12 )   1251 - 1252   1997年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    When aromatic halides were treated with alkylmagnesium reagents (which have beta-hydrogens) and a catalytic amount of zirconocene dichloride, dehalogenation proceeded smoothly in high yields. The stoichiometric dehalogenation using dialkylzirconocenes also proceeded with high selectivities.

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  • Cu(I)/Pd(0)-catalyzed cross-coupling reaction of alkynylsilanes with aryl or alkenyl triflates: "Sila"-Sonogashira-Hagihara coupling 査読

    Nishihara Y, Ikegashira K, Mori A, Hiyama T

    Chemistry Letters   ( 12 )   1233 - 1234   1997年

  • Copper(I) salt promoted homo-coupling reaction of organosilanes 査読

    Ikegashira K, Nishihara Y, Hirabayashi K, Mori A, Hiyama T

    Chemical Communications   ( 11 )   1039 - 1040   1997年

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  • TBAHF(2) and TBAH(2)F(3) as activating agents of organosilanes 査読

    Mori A, Fujita A, Ikegashira K, Nishihara Y, Hiyama T

    Synlett   ( 6 )   693 - 694   1997年

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  • Copper(I) salt mediated 1,4-reduction of alpha,beta-unsaturated ketones using hydrosilanes 査読

    Mori A, Fujita A, Nishihara Y, Hiyama T

    Chemical Communications   ( 22 )   2159 - 2160   1997年

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  • Highly selective monofunctionalization of zirconacyclopentanes and dialkylzirconocene complexes 査読

    Y Nishihara, K Aoyagi, R Hara, N Suzuki, T Takahashi

    INORGANICA CHIMICA ACTA   252 ( 1-2 )   91 - 99   1996年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA LAUSANNE  

    Selective monofunctionalization was investigated for symmetrical zirconacyclopentanes or symmetrical dialkylzirconocenes. Reaction of zirconacyclopentanes, which were prepared by intermolecular coupling of two alkenes, or intramolecular cyclization of dienes, trienes or tetraenes on zirconium, with PPh(2)Cl or SnR(3)Cl (R = Me, Ph) gave monofunctionalized products in good to high yields with high selectivities. Even in the presence of 2 equiv, of PPh(2)Cl or SnR(3)Cl, only one Zr-carbon bond reacted. Treatment of zirconacycropentanes with methanol yielded monoprotonated complexes. Subsequent addition of halogen such as Br-2 and I-2 to these monoprotonated complexes gave highly selective monohalogenated products. Similar monoprotonation reactions proceeded for dialkylzirconocene or -hafnocene complexes. Reaction of Cp(2)MR(2) (M = Zr or Hf, R = alkyl or aryl) with alcohols afforded alkylalkoxyzirconocene or -hafnocene complexes, Cp(2)MR(OR') (M = Zr or Hf, R' = alkyl or aryl) in high yields with high selectivities. High selectivity of monofunctionalization using PPh(2)Cl, SnR(3)Cl or alcohols can be attributed to the different reactivities between monoalkylzirconocenes which are monofunctionalized products and zirconacyclopentanes or dialkylzirconocenes.

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  • Copper-mediated coupling of zirconacyclopentadienes with dihalo aromatic compounds. Formation of fused aromatic rings 査読

    T Takahashi, R Hara, Y Nishihara, M Kotora

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   118 ( 21 )   5154 - 5155   1996年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

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  • PRACTICAL AND SELECTIVE METHOD FOR PREPARATION OF CP(2)HFRCL AND CP(2)HFRR' 査読

    T TAKAHASHI, Y NISHIHARA, T ISHIDA

    CHEMISTRY LETTERS   ( 2 )   159 - 160   1995年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Practical method for preparation of Cp(2)HfRCl and Cp(2)HfRR' has been investigated. Mono(alkyl)hafnocene chloride complexes were selectively prepared by the following methods; (i) a reaction of Cp(2)HfR(OMe) with MeCOCl and (ii) a reaction of Cp(2)HfCl(2) with an excess of R(3)Al. Treatment of Cp(2)HfRCl with R'Al-3 led to an alkyl exchange reaction to form Cp(2)HfR'Cl. Mono(alkyl)hafnocene complexes prepared by (ii) reacted with one equiv of R'Li to give Cp(2)HfRR' (R not equal R') with a high selectivity.

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  • Oxidative Addition of 2-Haloalkene to Zirconocene 査読

    Tamotsu Takahashi, Martin Kotora, Reinald Fischer, Yasushi Nishihara, Kiyohiko Nakajima, Tamotsu Takahashi

    Journal of the American Chemical Society   117 ( 44 )   11039 - 11040   1995年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/ja00149a040

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書籍等出版物

  • 有機ジルコニウム化合物 (19.2.3)

    丸善出版  2015年 

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  • ハートウィグ 有機遷移金属化学(上)

    東京化学同人  2014年  ( ISBN:4807908502

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  • Applied Cross-Coupling Reactions (Lecture Notes in Chemistry 80)

    SpringerーVerlag  2012年 

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  • 高機能デバイス用耐熱性高分子材料の最新技術

    シーエムシー出版  2011年 

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  • 使える!有機合成反応241実践ガイド

    化学同人  2010年 

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  • 高性能蓄電池-設計基礎研究から開発・評価まで-

    株式会社 エヌ・ティー・エス  2009年 

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  • 最新リチウムイオン二次電池〜安全性向上および高機能性に向けた材料開発〜

    株式会社情報機構  2008年 

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  • 光学用透明樹脂における材料設計と応用技術

    株式会社技術情報協会  2007年 

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  • 液晶便覧

    丸善  2000年 

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▼全件表示

MISC

  • Transistor application of new picene-type molecules, 2,9-dialkylated phenanthro[1,2-b:8,7-b '] dithiophenes (vol 3, pg 2413, 2015)

    Yoshihiro Kubozono, Keita Hyodo, Hiroki Mori, Shino Hamao, Hidenori Goto, Yasushi Nishihara

    JOURNAL OF MATERIALS CHEMISTRY C   3 ( 12 )   2960 - 2960   2015年

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    記述言語:英語   出版者・発行元:ROYAL SOC CHEMISTRY  

    DOI: 10.1039/c5tc90044a

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  • π 共役系分子を用いる有機電界効果トランジスタの最前線 (共著)

    森裕樹, 西原康師

    高分子   63 ( 12 )   866 - 870   2014年

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  • Recent Progresses in Organic Field Effect Transistors Based on π-Conjugated Organic Molecules

    Hiroki Mori, Yasushi Nishihara

    Polymer   63 ( 12 )   866 - 870   2014年

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  • Alkynylboron compounds in organic synthesis

    Jiao Jiao, Yasushi Nishihara

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   721   3 - 16   2012年12月

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    記述言語:英語   掲載種別:書評論文,書評,文献紹介等   出版者・発行元:ELSEVIER SCIENCE SA  

    Alkynylboron compounds, consisting of alkynyl and boron moieties, can be categorized according to the substituents on the boron atom, such as alkynylboranes, -boronates, and -borates. In this review, the synthesis and reactions of alkynylboron compounds are systematically introduced. Alkynylpinacolato-boranes and alkynyltrifluoroborates are the most widely utilized classes in organic reactions, owing to their stability and ease of handling. Other alkynylboron compounds have also been developed as convenient substrates for various organic reactions. Thanks to the dedication of many chemists in this field, great advances of facile synthesis and wide utilization of alkynylboron compounds have been made with these versatile building blocks for diverse structures in organic synthesis. (C) 2012 Elsevier B. V. All rights reserved.

    DOI: 10.1016/j.jorganchem.2012.05.027

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  • Preparation, structures, and thermal reactivity of alkoxycarbonyl(cyano)palladium(II) complexes trans-Pd(CO-OR)(CN)(PPh3)(2) (R = Me, Et, Pr-n, Pr-i, Bu-n, Bu-t, and Bn) as intermediates of the palladium-catalyzed cyanoesterification of norbomene derivatives (vol 26, pg 4054, 2007)

    Yasushi Nishihara, Mitsuru Miyasaka, Yoshiaki Inoue, Tomoka Yamaguchi, Masaaki Kojima, Kentaro Takagi

    ORGANOMETALLICS   26 ( 21 )   5250 - 5250   2007年10月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/om700868x

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  • Preparation, characterization, and reactivities of novel boryloxorhodium complexes

    Y Nishihara, Y Nishide, K Osakada

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   224   U729 - U729   2002年8月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:AMER CHEMICAL SOC  

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  • Cleavage of esters bearing a coordinative group by the catalysis of rare earth trifluoromethanesulfonate.

    H Kajiro, S Mitamura, Y Nishihara, A Mori, T Hiyama

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   222   U97 - U97   2001年8月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:AMER CHEMICAL SOC  

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  • Bis[bis(methylthio)lithiomethyl]dimethylsilanes: A useful reagent for the synthesis of polysilacarbacycles via disilylation

    Masaki Shimizu, Masayuki Iwakubo, Yasushi Nishihara, Tamejiro Hiyama

    Tetrahedron Letters   39 ( 20 )   3193 - 3196   1998年5月

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    Bis[bis(methylthio)lithiomethyl]dimethylsilane was generated from bis[bis(methylthio)methyl]dimethylsilane by deprotonation with t-BuLi in THF and allowed to react with various dichloro(poly)silanes to give the corresponding 4- to 7-membered polysilacarbacycles in moderate to good yields. The methylthio groups in the cyclized products were readily removed by radical reduction with Bu3SnH.

    DOI: 10.1016/S0040-4039(98)00457-2

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  • Alkylation methodology for the synthesis of 1,4-disilacyclohexanes using α,α'-dilithiated silanes

    Masaki Shimizu, Masayuki Iwakubo, Yasushi Nishihara, Tamejiro Hiyama

    Tetrahedron Letters   39 ( 20 )   3197 - 3200   1998年5月

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    The double alkylation of bis[2-(2-lithio-1,3-dithian)-yl]diorganosilane with bis(bromomethyl)diorganosilanes proceeds smoothly in good yields in a mixture of THF-hexamethylphosphoric trianide (HMPA) or THF-1,1,3,3- tetramethylurea (TMU) to give 1,4-disilacyclohexanes whose conformation was shown to be a twist-boat on the basis of X-ray analysis.

    DOI: 10.1016/S0040-4039(98)00458-4

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  • Novel cage polycarbosilanes. Preparation and characterization of dodecamethyl-2,3,5,6,7,8-hexasilabicyclo[2.2.2]octane and its derivatives

    Masaki Shimizu, Naoko Inamasu, Yasushi Nishihara, Tamejiro Hiyama

    Chemistry Letters   1145 - 1146   1998年1月

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    2,2,3,3,5,5,6,6,7,7,8,8-Dodecamethyl-2,3,5,6,7,8-hexasilabicyclo[2.2.2] octane (1) was synthesized for the first time via three steps in 56% overall yield through triple silylation with three dichlorodimethyldisilane molecules of two trianionic molecules derived from bis(phenylthio)methane. The molecular structure of 1 was shown to be slightly distorted from an ideal bicyclo-[2.2.2]octane skeleton by X-ray analysis. The derivatization of 1 and UV spectra of those compounds are described.

    DOI: 10.1246/cl.1998.1145

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  • Reaction of alkenylzirconocenes with dialkylzirconocenes: Unexpected formation of bimetallic (mu-alkynyl)zirconocene complexes

    T Takahashi, Y Nishihara, WH Sun, R Fischer, K Nakajima

    ORGANOMETALLICS   16 ( 10 )   2216 - 2219   1997年5月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    Reaction of alkenylzirconocenes Cp2ZrX-(MeC=CH2) (X = Cl, Br) with dialkylzirconocenes Cp-2-ZrR2 (R = Me, Et, Bu) yielded the unexpected bimetallic zirconocene complexes Cp2Zr(mu-X)(mu-C drop CCH3)ZrCp2 (X = Cl, Br). Its structure (X = Cl) was determined by X-ray crystallography. The monitoring of the reaction of Cp2ZrBu2 with Cp2ZrBr(MeC=CH2) revealed that the first step of this reaction was an exchange reaction of the Bu and Br groups.

    DOI: 10.1021/om960414u

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講演・口頭発表等

  • クロスカップリングを利用するフェナセン型分子の合成と電子エネルギーデバイスへの応用

    第29回万有札幌シンポジウム  2017年 

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  • Effects of alkyl side-chains and molecular weights on photovoltaic property in phenanthrodithiophene-based semiconducting polymers

    PACCON2017  2017年 

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  • 含硫黄フェナセン型分子の開発と有機電子エネルギーデバイス素子への応用

    第43回中国四国地区高分子講座  2017年 

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  • Development of High-Performance Organic Photovoltaic Cells Containing the Phenanthrodithiophene (PDT) Unit

    E-MRS (European Materials Research Society) 2016 Fall  2016年 

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  • Synthesis of Substituted Picenes through Pd-Catalyzed Cross-Coupling Reaction/Annulation Sequences and Their Physicochemical Properties

    International Symposium on Frontiers of Organometallic Chemistry  2013年 

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  • Highly Regio- and Stereoselective Synthesis of Multi-substituted Olefins from Alkynylboronates

    International Symposium of Homogenous Reactivity  2013年 

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  • クロスカップリング反応を用いるフェナセン型分子の合成と物性

    分子研シンポジウム  2013年 

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  • パラジウム触媒によるノルボルナジエンのシアノエステル化反応の開発と開環メタセシス重合によるポリシクロオレフィンの合成

    高分子学会中国四国支部 高分子研究科  2012年 

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  • Highly Selective Synthesis of Multi-substituted Olefins through Carbozirconation of Alkynylboronates and Sequential Cross-Couplings

    2nd International Conference on Molecular & Functional Catalysis (ICMFC-2),  2012年 

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  • 遷移金属を用いるカルボメタル化による選択的多置換オレフィンの合成

    近畿化学協会 有機金属部会平成22年度第4回例会  2011年 

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  • アルキニルボロン酸エステルのカルボジルコネーションとそれに続く根岸および鈴木-宮浦カップリングによる多置換オレフィン類の位置および立体選択的合成

    有機合成化学協会中国四国支部 ミニシンポジウム2011 in 愛媛  2011年 

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  • 開環メタセシス重合とそれに続く水素化によるシアノ基とエステル基を同時に有するポリノルボルネンの合成

    第60回高分子討論会  2011年 

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  • Highly Regio- and Stereoselective Synthesis of Multi-alkylated Olefins by Zirconocene-Mediated Transformation of 1-Alkynylboronates and Sequential Negishi and Suzuki-Miyaura Cross-Coupling Reactions

    14th Asian Chemical Congress (14th ACC)  2011年 

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  • Highly Efficient and Selective Synthesis of Multisubstituted Olefins from Alkynylboronates Mediated by a Zirconocene Complex

    The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)  2010年 

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  • Zirconocene-Mediated Highly Regio- and Stereoselective Synthesis of Multi-substituted Olefins from Alkynylmetallic Species

    The 6th International Symposium on Integrated Synthesis (ISIS-6)  2010年 

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  • Cross-Coupling Reactions of Aryl Halides with Alkynylsilanes Catalyzed by Palladium and Copper

    The 16th Malaysian Chemical Congress (16MCC), Kuala Lumpur  2010年 

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  • Synthesis of Doubly Functionalized Norbornenes and Ru-Catalyzed Ring-Opening Metathesis Polymerization

    China-Japan Symposium on Catalytic Organic Synthesis  2010年 

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  • Highly Regio- and Stereoselective Synthesis of Multi-substituted Olefins from Alkynylmetallic Species and Its Application toward Anti-cancer Agents

    第3回 高度医療都市を創出する未来技術国際シンポジウム-抗がん剤・抗感染症創薬のための標的分子探求-  2010年 

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  • 銅触媒によるアルキニルシランとヨウ化アリールの交差カップリング反応

    第57回有機金属化学討論会  2010年 

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  • Palladium/Copper-Cocatalyzed Sonogashir-Type Cross-Coupling Reactions of Aryl Halides with Alkynylsilanes via a Direct Carbon-Silicon Bond Cleavage

    The 24th International Conference on Organometallic Chemistry (ICOMC2010)  2010年 

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  • Palladium/Copper-Catalyzed Sila-Sonogashira Cross-Coupling Reactions of Aryl Halides with Alkynylsilanes via a Direct C-Si Bond Activation under a Neutral Condition

    11th Tetrahedron Symposium  2010年 

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  • パラジウム錯体を触媒として用いるシアノエステル化反応と反応機構の解明

    大阪市立大学談話会  2010年 

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  • パラジウム触媒によるノルボルネン類のシアノエステル化反応の開発と新規電子光学ポリマー合成への応用

    有機化学研究会(白鷺セミナー)  2010年 

     詳細を見る

  • Synthesis of Doubly Functionalized Norbornenes and Control of the Polymer Molecular Weights by Living Ring-Opening Metathesis Polymerization

    Second Japan-Singapore Bilateral Symposium on Catalysis  2009年 

     詳細を見る

  • Synthesis and Optical Rotation of Chiral Doubly Functionalized Polar Polynorbornenes

    The First International Symposium of Chemistry and Biochemistry in East Asia  2009年 

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  • Reactions of Alkynylstannanes with a Zirconocene Complex

    The First International Symposium of Chemistry and Biochemistry in East Asia  2009年 

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  • ジルコニウム錯体を用いる乳癌の治療薬タモキシフェンの効率的合成

    第2回高度医療都市を創出する未来技術国際シンポジウム~先端テクノロジーの総合戦略 がんと感染症を考える~  2009年 

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  • ジルコノセン錯体を用いる立体選択的アルケニルシラン合成と交差カップリング反応における置換基効果

    日本化学会第89春季年会  2009年 

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  • パラジウム触媒を用いるアルキニルシランとヨウ化アリールの交差カップリング反応

    日本化学会第89春季年会  2009年 

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  • ジルコノセン錯体とアルキニルシランを用いる高選択的多置換アルケニルシランの合成

    日本化学会第89春季年会  2009年 

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  • コバルト触媒を用いる根岸型アルキル-アリールクロスカップリング

    日本化学会第89春季年会  2009年 

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  • Palladium-Catalyzed Cyanoesterification of Norbornenes and Mechanistic Implications

    Symposium in Commemoration of International Exchange Agreement between Faculty of Science, University of Copenhagen, Denmark and Graduate School of Natural Science and Technlogy, Okayama University  2009年 

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  • Palladium-catalyzed sila-Sonogashira Cross-Coupling Reactions of Alkynylsilanes with Aryl Iodides under Neutral Conditions

    The First International Symposium of Chemistry and Biochemistry in East Asia  2009年 

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  • Synthesis and Examination of polymerization activity of Nickel(II) Complexes Tethered by Nitrogen-Oxygen Bidentate Ligand

    The First International Symposium of Chemistry and Biochemistry in East Asia  2009年 

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  • 遷移金属錯体による結合活性化法の開発と機能性分子合成への応用

    第26回有機合成化学セミナー  2009年 

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  • Highly Efficient and Selective Synthesis of Anticancer Agent Tamoxifen Mediated by a Zirconocene Complex

    13th Asian Chemical Congress (13th ACC)  2009年 

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  • 二置換型極性ノルボルネンのHPLC による光学分割と開環メタセシス重合によるキラルポリマーの合成

    第56回有機金属化学討論会  2009年 

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  • ジルコノセン錯体とアルキニルスズ化合物の反応

    日本化学会第89春季年会  2009年 

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  • ジルコニウム錯体を用いる乳癌の治療薬タモキシフェンの効率的合成

    第2回高度医療都市を創出する未来技術国際シンポジウム〜先端テクノロジーの総合戦略 がんと感染症を考える〜  2009年 

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  • ジルコノセン錯体と有機ホウ素化合物を用いる効率的かつ高選択的多置換オレフィン合成

    第93回有機合成シンポジウム  2008年 

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  • Palladium-Catalyzed Thioesterification with Arylthioformates across Norbornadiene

    Taiwan-Japan International Symposium on Organic Chemistru and Molecular Science  2008年 

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  • 乳癌の抗癌剤タモキシフェンの効率的全合成

    高度医療都市を創出する未来技術シンポジウム〜先端テクノロジーの総合戦略 がんと感染症を考える〜  2008年 

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  • Synthesis and Structural Analysis of Nickel(II) Complexes Tethered by Nitrogen-Oxygen Bidentate Ligands

    Taiwan-Japan International Symposium on Organic Chemistru and Molecular Science  2008年 

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  • Palladium-Catalyzed Cyanoesterification of Norbornenes and Its Application to Opto-electronic Polymers

    Taiwan-Japan International Symposium on Organic Chemistru and Molecular Science  2008年 

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  • パラジウム触媒を用いるノルボルナジエンのチオエステル化反応

    日本化学会第88春季年会  2008年 

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  • ジルコノセン(II) 錯体とアルキニルシランの反応

    日本化学会第88春季年会  2008年 

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  • 光学活性2置換型極性ポリノルボルネン類の合成と旋光性

    日本化学会第88春季年会  2008年 

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  • 二置換型極性ノルボルネンの合成およびリビング開環メタセシス重合によるポリマーの分子量制御

    日本化学会第88春季年会  2008年 

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  • 新規トリポッド配位子を有するロジウム触媒によるアリール亜鉛化合物のアルキル化

    日本化学会第88春季年会  2008年 

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  • ロジウム触媒を用いるアリール亜鉛化合物の酸化的カルボニル化によるジアリールケトン合成

    日本化学会第88春季年会  2008年 

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  • Synthesis of Unsymmetrical Diarylethynes by the Cross-Coupling Reaction ofAlkynylsilanes with Aryl Chlorides

    The 15th International Symposium on Organosilicon Chemistry  2008年 

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  • Efficient Synthesis of an Anti-cancer Agent, (Z)-Tamoxifen from an Alkynylboronate Mediated by a Zirconocene Complex

    Third International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability  2008年 

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  • パラジウム触媒によるアルキニルシランと塩化アリールのシラ薗頭カップリング反応

    第55回有機金属化学討論会  2008年 

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  • 酸素-窒素型二座配位子を有するニッケル(II)錯体の合成と構造解析

    第55回有機金属化学討論会  2008年 

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  • 根岸型アルキル-アリールクロスカップリング:配位性官能基を有するホスフィン配位子によるβ-水素脱離の抑制

    第55回有機金属化学討論会  2008年 

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  • Zirconocene-Mediated Highly Efficient and Selective Synthesis of Multisubstituted Olefins from Alkynylboronates and Its Application

    The 13th International Coference on Boron Chemistry (ImeBoron XIII),  2008年 

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  • Synthesis and Thermal Properties of Novel Polynorbornenes by Ru-Initiated Ring-Opening Metathesis Polymerization and the Subsequent Ru-Catalyzed Hydrogenation

    The 23rd International Coference on Organometallic Chemistry (ICOMC2008)  2008年 

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  • パラジウム触媒によるノルボルネン類のシアノエステル化反応と新規機能性光学材料への応用 (依頼講演)

    第23回若手化学者のためのセミナー(化学道場)  2007年 

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  • Zirconocene-Mediated Highly Efficient and Selective Synthesis of Multisubstituted Olefins from Alkynylboronates

    The 11th Osaka City University International Conference "New Horizons of Molecular Science Dispatched from Asia"  2007年 

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  • Synthesis of Novel Cycloolefin Polymers by Ru-Initiated Ring-Opening Metathesis Polymerization and Subsequent Ru-Catalyzed Hydrogenation of Doubly Functionalized Norbornenes with Both Cyano and Ester Groups

    The 14th Organometallic Chemistry towards Organic Synthesis (OMCOS-14)  2007年 

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  • Zirconocene-Mediated Highly Selective and Facile Synthesis of 1,2-Diaryl-1-butenes from Alkynylboronates

    Second International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability International Conference on Asymmetric Organocatalysis  2007年 

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  • 含ホウ素有機―無機複合ポリマーのリチウムイオン伝導性と全固体二次電池への応用

    日本化学会第87春季年会  2007年 

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  • ジルコノセン錯体を用いる1,2-ジアリールブテンの位置および立体選択的合成

    日本化学会第87春季年会  2007年 

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  • ルテニウムヒドリド触媒による二置換型極性ポリノルボルネン類の水素添加

    日本化学会第87春季年会  2007年 

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  • 二置換型極性ポリノルボルネン類のエステル基上の置換基効果

    日本化学会第87春季年会  2007年 

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  • オレフィンメタセシスにより得られた2官能性アリールボロン酸をモノマーとするポリマー電解質の合成

    日本化学会第87春季年会  2007年 

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  • 新規テトラアリールペンタボラート骨格を含むリチウムイオン2次電池のための有機―無機複合ポリマー電解質の合成

    日本化学会第87春季年会  2007年 

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  • ロジウム触媒を用いるアリール亜鉛化合物とホスホリル基を持つアルキルヨウ化物とのクロスカップリング反応

    日本化学会第87春季年会  2007年 

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  • Zirconocene-Mediated Total Synthesis of (Z)-Tamoxifen Starting from 1-Alkynylboronates

    3rd China-Japan Symposium On Chemistry  2007年 

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  • パラジウム触媒を用いるノルボルナジエンへのチオエステル化反応

    2007年日本化学会西日本大会  2007年 

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  • ルテニウムヒドリド触媒による二置換型極性ポリノルボルネン類の水素化反応と置換基効果

    2007年日本化学会西日本大会  2007年 

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  • 触媒的クロスカップリングによるホスホリル置換アルキルアレーン類の合成

    2007年日本化学会西日本大会  2007年 

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  • ロジウム触媒を用いるアリール金属化合物の酸化的カップリング

    2007年日本化学会西日本大会  2007年 

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  • ジルコノセン錯体による多置換オレフィン類の位置選択的合成

    2007年日本化学会西日本大会  2007年 

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  • パラジウム触媒によるノルボルネン類のシアノエステル化の中間体-アルコキシ(シアノ)パラジウム(II)錯体の合成と構造

    第54回有機金属化学討論会  2007年 

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  • ルテニウム触媒による二置換型極性ポリノルボルネン類の水素添加とエステル基上の置換基効果

    第54回有機金属化学討論会  2007年 

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  • ジルコノセン錯体とアルケニルホウ素化合物を用いる多置換オレフィン類の効率的かつ高選択的合成

    第54回有機金属化学討論会  2007年 

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  • ルテニウムカルベン錯体を開始剤として用いる2官能性極性ノルボルネン誘導体のリビング開環メタセシス重合

    第53回有機金属化学討論会  2006年 

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  • ノルボルネン類のシアノエステル化反応とその生成物をモノマーとする開環メタセシス重合反応〜新規光学系材料の実用化を目指して〜

    若手研究者の会  2006年 

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  • 二置換型極性ノルボルネン類の合成と重合反応

    第55回高分子学会年次大会  2006年 

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  • リチウムイオン電池の大型化を目指した含ホウ素有機-無機複合固体電解質の創製

    「自動車用リチウムイオン二次電池の高出力化,長寿命化と安全性評価」講習会  2006年 

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  • 二置換型極性ノルボルネン類の開環メタセシス重合

    日本化学会第86春季年会  2006年 

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  • アルコキシカルボニル(シアノ)パラジウム (II) 錯体の合成と反応

    日本化学会第86春季年会  2006年 

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  • アルコキシカルボニル(シアノ)パラジウム (II) 錯体とノルボルナジエンの反応

    第56回錯体化学討論会  2006年 

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  • パラジウム触媒を用いるノルボルナジエンのシアノエステル化反応

    日本化学会第86春季年会  2006年 

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  • アリール亜鉛化合物を用いる官能基をもつアリールアレンの合成

    日本化学会第86春季年会  2006年 

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  • ロジウム触媒を用いるアリール亜鉛化合物とハロゲン化アリールとのクロスカップリング

    日本化学会第86春季年会  2006年 

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  • パラ-フェニレンジ亜鉛化合物の逐次的クロスカップリング反応:配位子効果の検討

    日本化学会第86春季年会  2006年 

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  • 極性シクロオレフィンポリマーの開発を目指した置換ノルボルネン類の合成と反応性

    「シクロオレフィンポリマーの特性と応用」講習会  2006年 

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  • 新規機能性光学材料を指向したシアノ基とエステル基を同時に有するポリシクロオレフィンの合成

    2006年日本化学会西日本大会 2H06  2006年 

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  • Synthesis of Doubly Functionalized Polar Norbornenes by the Palladium-Catalyzed Cyanoesterification

    The 10th International KYOTO Conference on New Aspects of Organic Chemistry (IKCOC-10), PA-016  2006年 

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  • フェニレンジ亜鉛化合物への求電子剤の逐次的導入

    日本化学会第85春季年会  2005年 

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  • ロジウム触媒を用いるアリール亜鉛化合物のアルキル化

    日本化学会第85春季年会  2005年 

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  • 銅塩を用いるアルキニルボロン酸エステルと酸クロリドの交差カップリング反応

    日本化学会第85春季年会  2005年 

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  • 銅塩を用いるアルキニルボロン酸エステル類のホモカップリング反応

    日本化学会第85春季年会  2005年 

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  • アルキニルボロン酸エステルと銅塩の反応によるアルキニル銅種の生成とその反応性

    日本化学会第85春季年会  2005年 

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  • 銅塩とパラジウム触媒を用いるアリールボロン酸と酸クロリドの交差カップリング反応

    日本化学会第85春季年会  2005年 

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  • リチウムイオン電池の電解質を指向した含ホウ素有機―無機複合ポリマーの合成と物性(2)

    第46回電池討論会  2005年 

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  • リチウムイオン電池の電解質を指向した含ホウ素有機―無機複合ポリマーの合成と物性(1)

    第46回電池討論会  2005年 

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  • パラジウム触媒を用いるノルボルネン類のシアノエステル化反応

    第52回有機金属討論会  2005年 

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  • Copper-Mediated Homocoupling Reactions of Alkynylboronates Affording Symmetrical Conjugate Diynes

    12th International Conference on Boron Chemistry (MEBORON-XII)  2005年 

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  • A Preparative Synthetic Method of Ketones by Cross-Coupling Reactions of Acid Chlorides with Organoboron Compounds

    The 13rd Organometallic Chemistry towards Organic Synthesis (OMCOS-13)  2005年 

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  • アリール配位子へのフッ素原子の導入による重要中間体の単離と構造解析

    第11回フッ素化学セミナー「含フッ素リガンドの展開」  2004年 

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  • ホスフィド架橋をもつ環状三核ヒドリド白金錯体と有機ケイ素化合物の反応

    第84日本化学会春季年会  2004年 

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  • アリール(ヒドロキソ)パラジウム(II) 錯体と有機ホウ素化合物の反応

    第84日本化学会春季年会  2004年 

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  • メトキソおよびヒドロキソロジウム(I) 錯体とアリールボロン酸エステルの反応

    第84日本化学会春季年会  2004年 

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  • ホスフィド架橋をもつ環状三核ヒドリド白金錯体と有機ホウ素化合物との反応

    第84日本化学会春季年会  2004年 

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  • 遷移金属錯体と有機ホウ素化合物の反応—トランスメタル化反応を鍵として

    第36回有機金属化学若手の会夏の学校  2003年 

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  • Synthesis and Structural Characterization of the First Unsymmetrical Diarylpalladium Complexes trans-Pd(C6F5)(2,4,6-C6F3H2)(PEt3)2 from Arylboronic Acid 2,4,6-C6F3H2B(OH)2 and trans-PdI(C6F5)(PEt3)2

    The 12nd Organometallic Chemistry directed towards Organic Synthesis (OMCOS-12)  2003年 

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  • 低原子価白金錯体と二級ホスフィンとの反応によるジホスフィド架橋多核白金(II) 錯体の合成

    第81日本化学会春季年会  2003年 

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  • アリール(ヨード)パラジウム(II) および白金(II)錯体とアリールボロン酸の反応におけるホスフィン類の効果

    第81日本化学会春季年会  2003年 

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  • アリーロキソまたはメトキソロジウム(I) 錯体とボロン酸エステルとの反応

    第81日本化学会春季年会  2003年 

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  • アリールオキソロジウム(I) 錯体とアリールボロン酸との反応による新規ペンタボラートアニオンの合成

    第81日本化学会春季年会  2003年 

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  • アリール(トリフラート)パラジウム(II)錯体とアリールボロン酸の反応による非対称ジアリールパラジウム(II)錯体の生成

    第53回錯体化学討論会  2003年 

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  • アルコキソロジウム(I) 錯体 [Rh(OR)(cod)]2 (R = Me, Et, tBu) とアリールボロン酸エステルとの反応

    第53回錯体化学討論会  2003年 

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  • 架橋有機リン配位子をもつ直線状白金多核錯体の合成

    第53回錯体化学討論会  2003年 

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  • アリール(ハロゲノ)白金(II) 錯体と有機ホウ素化合物の反応におけるホスフィン配位子の効果

    第53回錯体化学討論会  2003年 

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  • Synthesis of Tetraarylpentaborates from Reaction of Arylboronic Acids with an Aryloxorhodium Complex.

    35th International Conference on Coordination Chemistry  2002年 

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  • アリーロキソまたはメトキソロジウム(I) 錯体とボロン酸エステルとの反応

    第81日本化学会春季年会  2002年 

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  • 白金触媒を用いるメチレンシクロプパン類の異性化反応

    第81日本化学会春季年会  2002年 

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  • ロジウム(I) ヒドリド錯体と1-メチレン-4-フェニル-スピロ[2.2]ペンタンとの反応

    第81日本化学会春季年会  2002年 

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  • ロジウム(I)アリーロキソ錯体とアリールボロン酸との反応によるスピロ型ボロキシナートアニオンの合成

    第81日本化学会春季年会  2002年 

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  • アリールオキソロジウム(I)錯体とアリールボロン酸との反応による含ホウ素アニオンの合成

    子研研究会,無機金属化学の展望―全元素化学を目指して  2002年 

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  • アリール(ハロゲノ)白金(II)錯体とアリールボロン酸の反応におけるトランスメタル化

    第52回錯体化学討論会  2002年 

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  • ロジウム(I)アリールオキソ錯体とアリールボロン酸エステルとの反応

    第52回錯体化学討論会  2002年 

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  • シリルロジウム(III) およびイリジウム(III) 錯体のケイ素—塩素結合生成反応—中心金属,シリル配位子による反応性の違い

    第47回有機金属化学討論会  2002年 

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  • Preparation, Characterization, and Reactivities of Novel Boryloxorhodium Complexes.

    The 224th ACS National Meeting  2002年 

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  • Rhodium(III) and Iridium(III) Complexes with Halo and Alkoxysilyl Ligands. Relative Stability of the Metal–Silicon Bond and Elimination of Halosilanes.

    20th International Conference on Organometallic Chemistry  2002年 

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  • Highly selective C-C bond activation of methylenecyclopropanes by transition metal complexes

    シンポジウム:有機金属化学の最先端  2002年 

     詳細を見る

  • Vaska 錯体とヒドロシラン類との反応におけるケイ素上の置換基の違いとクロロシランの還元的脱離速度に関する研究

    第7回ケイ素化学協会シンポジウム  2002年 

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  • メチレンシクロプロパンの化学–錯体から有機合成まで–,

    錯体化学若手の会ミニシンポジウム  2002年 

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  • 有機パラジウム錯体とアリールホウ素化合物の反応

    第52回錯体化学討論会  2002年 

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  • 選択的な3員環の開環を伴う1-メチレン-4-フェニル-スピロ[2.2]ペンタンとロジウム(I) ヒドリド錯体との反応

    第52回錯体化学討論会  2002年 

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  • ハロゲノ(ヒドリド)シリルロジウム(III) 錯体の安定性と反応性に及ぼすハロゲンの影響

    第6回ケイ素化学協会シンポジウム  2001年 

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  • 白金錯体を触媒とするメチレンシクロプロパン類のヒドロシリル化反応

    第47回有機金属化学討論会  2001年 

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  • リン配位子をもたないロジウム(I) 錯体と有機ボロン酸との反応

    第51回錯体化学討論会  2001年 

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  • アリーロキソおよびヒドロキソロジウム(I)錯体と有機ホウ素化合物との反応

    第51回錯体化学討論会  2001年 

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  • ロジウム(I)ヒドリド錯体と2,2-ジアルキル-1-メチレンシクロプロパンとの反応

    第79日本化学会春季年会  2001年 

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  • イリジウム(I)ヒドリド錯体と2,2-ジアルキル-1-メチレンシクロプロパンとの反応

    第79日本化学会春季年会  2001年 

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  • 2,2-ジアルキル置換メチレンシクロプロパンとロジウムおよびイリジウムヒドリド錯体との反応—ビニル錯体の生成と異性化—

    第51回錯体化学討論会  2001年 

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  • Ring-Opening Isomerization of Methylenecyclopropopanes into 1,3-Dienes Promoted by Transition Metal Hydrido Complexes.

    Post-OMCOS  2001年 

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  • 白金触媒によるメチレンシクロプロパン類のヒドロシリル化反応における中間錯体の単離と同定

    第51回錯体化学討論会  2001年 

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  • ロジウム(I)ヒドロキソ錯体と有機ボロン酸との反応

    第79日本化学会春季年会  2001年 

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  • 遷移金属錯体触媒を用いるメチレンシクロプロパン類のヒドロシリル化反応

    第79日本化学会春季年会  2001年 

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  • 白金(II)カチオン錯体へのシラノール上の有機基のトランスメタル化反応—ケイ素–炭素結合の活性化における機構の考察—

    第79日本化学会春季年会  2001年 

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  • 銅(I) 塩を用いるアルキニルシランのカップリング反応を利用するビスフェノールA誘導体ユニットを含む高分子の合成

    第78日本化学会春季年会  2000年 

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  • ロジウム (I)ヒドリド錯体とメチレンシクロプロパンの反応とその機構的考察

    第78日本化学会春季年会  2000年 

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  • アルキニル基のケイ素から銅へのトランスメタル化の機構的考察

    第78日本化学会春季年会  2000年 

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  • ロジウム(I)およびイリジウム(I)ヒドリド錯体を用いる1-メチレンシクロプロパン類の新規な炭素–炭素,炭素-水素結合の活性化

    第47回有機金属討論会  2000年 

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  • ロジウム(I)アリーロキシ錯体の有機金属化合物との反応

    第50回錯体化学討論会  2000年 

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  • 新しいシリルロジウム錯体の合成とアセチレンとの反応

    第50回錯体化学討論会  2000年 

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  • メチレンシクロプロパンの炭素–炭素結合の活性化を伴うロジウム(I)錯体上での配位子骨格変換反応

    第50回錯体化学討論会  2000年 

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  • 白金(II)錯体によるシラノールのケイ素–炭素結合の活性化と有機基のトランスメタル化反応

    第50回錯体化学討論会  2000年 

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  • Isolation of Intermediates of Ring-opening Isomerization of Methylenecyclopropanes Promoted by Rh(I) and Ir(I) Complexes..

    34th International Conference on Coordination Chemistry  2000年 

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  • シランジオールの合成とパラジウム触媒を用いるカップリング反応

    第78日本化学会春季年会  2000年 

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  • 3,3,3-トリフルオロプロピル基を有するシラノールの交差カップリングと Mizoroki-Heck 型反応

    第78日本化学会春季年会  2000年 

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  • New C-C and C-H Bond Activation of 1-Methylenecyclopropanes Promoted by Hydrido Complexes of Rh(I) and Ir(I).

    2000 International Chemical Congress of Pacific Basin Societies (Pacifichem ‘2000)  2000年 

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  • フッ化テトラブチルアンモニウムを活性化剤に用いる末端アルキンの交差カップリング反応

    第46回有機金属討論会  2000年 

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  • 同一分子内にアルキニルシランとトリフラートを有する化合物の交差カップリングを用いる重合反応

    第78日本化学会春季年会  2000年 

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  • アルキニルシランとアリールトリフラートの交差カップリング反応を利用する高分子合成

    第76日本化学会春季年会  1999年 

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  • 立体選択的ヒドロシリル化を利用する含ケイ素高分子の合成

    第76日本化学会春季年会  1999年 

     詳細を見る

  • パラジウム触媒を用いるシラノールの交差カップリング反応

    第76日本化学会春季年会  1999年 

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  • シラノールおよび有機スズ化合物を用いたMizoroki-Heck 型反応

    第76日本化学会春季年会  1999年 

     詳細を見る

  • ケイ素上にキラリティーを持つシラノールの合成と光学分割

    第76日本化学会春季年会  1999年 

     詳細を見る

  • フッ素の配位を利用したSc(OTf)3による脱アセチル化反応

    第76日本化学会春季年会  1999年 

     詳細を見る

  • アルキニルシランのホモカップリング反応を利用する高分子合成

    第76日本化学会春季年会  1999年 

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  • オレフィン・ホスフィン2座配位子をもつジルコノセン錯体の合成と構造

    第49錯体化学討論会  1999年 

     詳細を見る

  • 銅(I) 塩によるアルキニルシランのカップリング反応を利用する高分子合成

    第77日本化学会秋季年会  1999年 

     詳細を見る

  • シラノール,シランジオールを用いる炭素—炭素結合形成反応

    第46回有機金属討論会  1999年 

     詳細を見る

  • 銅(I) 塩を用いる有機ケイ素化合物のカップリング反応とトランスメタル化における機構的考察

    第46回有機金属討論  1999年 

     詳細を見る

  • Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions of Silanols

    The 216th ACS Meeting  1999年 

     詳細を見る

  • Homo- and Cross-Coupling Reactions of Alkynylsilanes Mediated by a Copper(I) Salt

    The 216th ACS Meeting  1999年 

     詳細を見る

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受賞

  • 日本学術振興会 科研費審査委員表彰

    2017年  

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    受賞国:日本国

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  • 平成29年度 岡山工学振興会 内山勇三科学技術賞

    2017年  

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    受賞国:日本国

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  • 2008年度有機合成化学奨励賞

    2009年  

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    受賞国:日本国

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  • 第88春季年会 優秀講演賞(産業)

    2008年  

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    受賞国:日本国

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  • 第1回岡山大学理学部教育貢献賞

    2007年  

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    受賞国:日本国

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  • 平成19年度岡山大学若手トップリサーチャー

    2007年  

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    受賞国:日本国

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  • 第15回有機合成化学協会研究企画賞(日本触媒)

    2003年  

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    受賞国:日本国

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担当授業科目

  • 反応化学特別講義Ⅱ (2021年度) 集中  - その他

  • 反応化学特論 (2021年度) 前期  - 月

  • 合成有機化学 (2021年度) 前期  - その他

  • 基礎有機化学 (2021年度) 1・2学期  - 金1,金2

  • 基礎有機化学 (2021年度) 3・4学期  - 金1,金2

  • 基礎有機化学1 (2021年度) 第1学期  - 金1,金2

  • 基礎有機化学1 (2021年度) 第3学期  - 金1~2

  • 基礎有機化学1 (2021年度) 第3学期  - 金1,金2

  • 基礎有機化学1 (2021年度) 第1学期  - 金1~2

  • 有機化学10 (2021年度) 第2学期  - 火1,火2

  • 有機化学9 (2021年度) 第1学期  - 火1,火2

  • 有機化学V (2021年度) 1・2学期  - 火1,火2

  • 機能有機化学演習 (2021年度) 通年  - その他

  • 自然科学入門1(化学) (2021年度) 第1学期  - 火3~4

  • 自然科学入門2(化学) (2021年度) 第2学期  - 火3~4

  • 合成有機化学 (2020年度) 前期  - その他

  • 基礎有機化学1 (2020年度) 第1学期  - 金1,金2

  • 基礎有機化学1 (2020年度) 第3学期  - 金1,金2

  • 基礎有機化学1 (2020年度) 第3学期  - 金1,金2

  • 基礎有機化学1 (2020年度) 第1学期  - 金1,金2

  • 有機化学10 (2020年度) 第2学期  - 火1,火2

  • 有機化学3 (2020年度) 第3学期  - 火3,火4

  • 有機化学4 (2020年度) 第4学期  - 火3,火4

  • 有機化学9 (2020年度) 第1学期  - 火1,火2

  • 有機化学II (2020年度) 3・4学期  - 火3,火4

  • 有機化学V (2020年度) 1・2学期  - 火1,火2

  • 有機金属触媒化学 (2020年度) 前期  - 火3,火4

  • 機能有機化学演習 (2020年度) 前期

  • 機能有機化学演習 (2020年度) 通年  - その他

  • 機能有機化学演習 (2020年度) 前期

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