Updated on 2024/03/13

写真a

 
OSHIKI Toshiyuki
 
Organization
Faculty of Environmental, Life, Natural Science and Technology Lecturer
Position
Lecturer
Profile
【職歴】
1991年4月-1995年3月:
三菱化成(株)横浜総合研究所
1996年4月-1998年10月:
日本学術振興会特別研究員
1998年11月-2005年3月:
岡山大学工学部
2005年4月-現在:
岡山大学大学院自然科学研究科 (工学部化学生命系学科)

【岡山大学における共同利用スペースの利用の歴史】
2007年4月-2008年12月
津島キャンパス 新技術研究センター
(新エネルギー・産業技術総合開発機構(NEDO) 産業技術研究助成事業(若手研究グラント)の推進のため)
2008年12月-現在
芳賀キャンパス 産学官融合センター
(NEDO産業技術研究助成事業の推進のため(2010年11月まで))
(NEDOエコイノベーション推進事業の推進のため(2009年6月-2010年2月))
(民間企業との共同研究の推進のため(-現在))
External link

Degree

  • 理学修士 ( 千葉大学 )

  • Doctor (Science) ( Osaka University )

Research Interests

  • 錯体触媒プロセス

  • Homogeneous Catalysis

Research Areas

  • Nanotechnology/Materials / Green sustainable chemistry and environmental chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Inorganic/coordination chemistry

  • Manufacturing Technology (Mechanical Engineering, Electrical and Electronic Engineering, Chemical Engineering) / Catalyst and resource chemical process

Education

  • Osaka University    

    - 1998

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  • Osaka University   基礎工学研究科   化学系

    - 1998

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    Country: Japan

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  • Chiba University    

    - 1989

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  • Chiba University   理学部   化学

    - 1989

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    Country: Japan

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Research History

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

    2002

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  • - 岡山大学自然科学研究科 講師

    2002

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Professional Memberships

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Committee Memberships

  • 石油学会   正会員、中国四国支部役員会委員  

    2021   

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    Committee type:Academic society

    石油学会

  • 石油学会   正会員、中国四国支部役員会委員  

    2020   

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    Committee type:Academic society

    石油学会

  • 高分子学会   正会員  

    2014   

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    Committee type:Academic society

    高分子学会

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  • 触媒学会   西日本地区幹事  

    2011   

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    Committee type:Academic society

    触媒学会

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  • 石油学会   正会員、中国四国支部役員会委員  

    2010   

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    Committee type:Academic society

    石油学会

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  • 石油学会   正会員、中国四国支部役員会委員  

    2009   

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    Committee type:Academic society

    石油学会

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  • 石油学会   正会員、中国四国支部役員会委員  

    2008   

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    Committee type:Academic society

    石油学会

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  • 日本化学事業開発協会   会員  

    2002   

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    Committee type:Academic society

    日本化学事業開発協会

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  • アメリカ化学会(American Chemical Society)   正会員  

    1993 - 2011   

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    Committee type:Academic society

    アメリカ化学会(American Chemical Society)

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  • 有機合成化学協会   正会員 編集協力委員  

       

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    Committee type:Academic society

    有機合成化学協会

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Papers

  • Synthesis and Optical Properties of Dithieno-1,4-Thiaborins Bearing Electron-Donating Amino Groups

    Tomohiro Agou, Shota Hayama, Naoya Takano, Shigeyuki Yamada, Tsutomu Konno, Toshiyuki Oshiki, Hidehito Komatsuzaki, Hiroki Fukumoto

    Bulletin of the Chemical Society of Japan   2024.2

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    Publishing type:Research paper (scientific journal)   Publisher:Oxford University Press (OUP)  

    Abstract

    Dibenzo-1,4-heteraborins and their π-extended derivatives have been paid increased attention to because of their potential as optical and electronic functional materials such as organic electroluminescence emitters. Meanwhile, 1,4-heteraborin compounds with heteroaromatic ring systems have remained scarce, even though Liu et al. recently reported the synthesis, properties and functionalization of dithieno-1,4-thiaborins (DTTBs). In this work, DTTBs with 10H-phenothiazine-10-yl (Pz), 9H-carbazol-9-yl (Cz), and p-(Ph2N)C6H4 groups as electron-donating amino groups at the α-positions of the thiophene moieties were synthesized using palladium-catalyzed coupling reactions. X-Ray crystallographic analysis revealed the molecular structure of a DTTB substituted with Pz groups. This analysis showed that the two Pz moieties adopted extra- (quasi-axial) conformations. The Cz and p-(Ph2N)C6H4 substituted DTTBs showed red-shifted absorption and emission when compared to the original DTTBs. This shift is due to donor–acceptor interactions between the amino groups and the DTTB cores. The Pz-substituted DTTB exhibited dual fluorescence emissions, originating from the locally-excited (LE) and twisted intramolecular charge transfer (TICT) states. The intensity and nature of these emissions varied based on solvent polarity, temperature, and viscosity, suggesting the potential of the Pz-substituted DTTB to act as a fluorescent environment sensor.

    DOI: 10.1093/bulcsj/uoae014

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  • A Practical Method for the Measurement of 183W NMR Signals in Solution: Challenge to Multinuclear Solution NMR Invited

    Toshiyuki Oshiki

    58 ( 1 )   2023.7

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (bulletin of university, research institution)  

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  • A Practical Method for the Measurement of 183W NMR Signals in Solution: Challenge to Multinuclear Solution NMR Invited

    55 ( 1 )   16 - 23   2023.6

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  • Synthesis and characterization of a polystyrene-type polymer bearing a cyclic perfluoroalkylene group Reviewed

    Tatsuro Hisa, Yasunori Kanno, Tomohiro Shirai, Toshiyuki Oshiki, Yoshiyuki Mizuhata, Norihiro Tokitoh, Hiroki Fukumoto, Tomohiro Agou

    Polymer   265   125588 - 125588   2022.12

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    DOI: 10.1016/j.polymer.2022.125588

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  • Synthesis of perfluoroalkylene-vinylene-arylene copolymers via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with dihalogenated arylene monomers Reviewed

    Hiroto Tsukada, Tatsuro Hisa, Tomohiro Shirai, Toshiyuki Oshiki, Yoshiyuki Mizuhata, Norihiro Tokitoh, Hiroki Fukumoto, Tomohiro Agou

    Journal of Fluorine Chemistry   261-262   110033 - 110033   2022.9

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    DOI: 10.1016/j.jfluchem.2022.110033

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  • Presence of Microplastics in Four Types of Shellfish Purchased at Fish Markets in Okayama City, Japan. Reviewed

    Kenichi Yamamoto, Toshiyuki Oshiki, Hiroko Kagawa, Masayoshi Namba, Masakiyo Sakaguchi

    Acta medica Okayama   75 ( 3 )   381 - 384   2021.6

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    The worldwide microplastic pollution in our environment is a matter of great concern. Harmful effects of plastics have been reported in various types of organisms including murine animals. We examined the presence of microplastics in four types of shellfish purchased from fish markets in Okayama, Japan and served to the public: short-neck clam (Ruditapes philippinarum, asari in Japanese), hard-shell clam (Meretrix lusoria, hamaguri), brackishwater clam (Cyrenidae, shijimi), and oyster (Crassostrea gigas, kaki). Our analyses demonstrated that approx. 3 pieces of microplastics were present per single shellfish, based on the division of the total number of pieces of microplastic obtained from all 4 types of shellfish by the total number of shellfish examined. Since health problems in humans due to microplastics have not yet been confirmed, further examinations of the effects of ingested microplastics are needed.

    DOI: 10.18926/AMO/62234

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  • Cytotoxic Effects of Alcohol Extracts from a Plastic Wrap (Polyvinylidene Chloride) on Human Cultured Liver Cells and Mouse Primary Cultured Liver Cells. Reviewed

    Ken-Ichi Yamamoto, Hiroko Kagawa, Sakae Arimoto, Xian Wen Tan, Kento Yasui, Toshiyuki Oshiki, Masakiyo Sakaguchi

    Acta medica Okayama   74 ( 4 )   327 - 334   2020.8

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    An increasing accumulation of microplastics and further degraded nanoplastics in our environment is suspected to have harmful effects on humans and animals. To clarify this problem, we tested the cytotoxicity of two types of plastic wrap on human cultured liver cells and mouse primary cultured liver cells. Alcohol extracts from plastic wrap, i.e., polyvinylidene chloride (PVDC), showed cytotoxic effects on the cells. Alcohol extracts of polyethylene (PE) wrap were not toxic. The commercially available PVDC wrap consists of vinylidene chloride, epoxidized soybean oil, epoxidized linseed oil as a stiffener and stabilizer; we sought to identify which component(s) are toxic. The epoxidized soybean oil and epoxidized linseed oil exerted strong cytotoxicity, but the plastic raw material itself, vinylidene chloride, did not. Our findings indicate that plastic wraps should be used with caution in order to prevent health risks.

    DOI: 10.18926/AMO/60371

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  • Structural Characterization and Unique Catalytic Performance of Silyl-Group-Substituted Geminal Dichromiomethane Complexes Stabilized with a Diamine Ligand Reviewed

    Masahito Murai, Ryuji Taniguchi, Naoki Hosokawa, Yusuke Nishida, Hiroko Mimachi, Toshiyuki Oshiki, Kazuhiko Takai

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   139 ( 37 )   13184 - 13192   2017.9

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    Stabilization by a silyl group on the methylene carbon and a diamine ligand led to the isolation of gem-dichromiomethane species. X-ray crystallography confirmed the identity of the structure of this rare example of reactive gem-dimetalloalkane species. The isolated gem-dichromiomethane complex acted as a storable silylmethylidene carbene equivalent, with reactivity that could be changed dramatically upon addition of a Lewis acid (ZnCl2) and a base (TMEDA) to promote both silylalkylidenation of polar aldehydes and silylcyclopropanation of nonpolar alkenes. Identification of a key reactive species also identified the catalytic version of these transformations and provided insights into the reaction mechanism. In contrast to Simmons-Smith cyclopropanation, the real reactive species for the current cyclopropanation was a chromiocarbene species, not a chromium carbenoid species.

    DOI: 10.1021/jacs.7b07487

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  • Industrial Application and Olefin Metathesis Catalyst Technologies for Reaction Injection Molding of Dicyclopentadiene Reviewed

    Michiru Kamada, Toshiyuki Oshiki

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   75 ( 2 )   19 - 28   2017.2

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

    Current technologies of DCP-RIM (reaction injection molding of dicyclopentadiene) are reviewed from an industrial point of view. The DCP-RIM provides high-impact, heat resistant, and insulating poly (dicyclopentadiene) thermoset resin via catalytic olefin metathesis. Control of chemical reactivities of the catalysts is one of the most important technologies for the DCP-RIM. The key properties of the catalysts are their good solubility in dicyclopentadiene and latency.
    Suitable tungsten or molybdenum-based catalyst systems have been developed and used for over 30 years. These catalyst systems are comprised of inorganic tungsten (or molybdenum) salt and an air-sensitive organoaluminum as an activator. In contrast, robust Grubbs type ruthenium-alkylidene catalysts are attracted great interest in the field of the DCP-RIM. Detailed structure and reactivities of the ruthenium catalysts for the DCP-RIM are summarized.

    DOI: 10.5059/yukigoseikyokaishi.75.111

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  • New Catalyst Technology for Industrial Production of Polydicyclopentadiene Molding

    OSHIKI TOSHIYUKI, KAMADA MICHIRU, NISHIOKA NAOKI

    山陽技術雑誌   61   10 - 14   2014.4

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  • 革新的プロセス開発の新展開 産業界と連携した革新性ある錯体触媒プロセスの開発

    押木俊之

    ケミカルエンジニヤリング   59 ( 2 )   93 - 100   2014.2

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  • PH effect on properties of surfactant-free oil-in-water emulsion prepared with oleic acid Reviewed

    Yuta Akizuki, Mikio Yoshida, Naoyuki Ishida, Toshiyuki Oshiki, Jun Oshitani

    Chemistry Letters   43 ( 5 )   604 - 606   2014

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    Size distribution, potential, and yield of surfactant-free oil-in-water (O/W) emulsion prepared with oleic acid were measured at various pHs after seven days from the emulsification. We found that the size distribution is almost the same regardless of pH from 9 to 3. The magnitude of potential and yield remains constant at pH from 9 to 6, and decreases at pH from 6 to 3. There is a correlation between the potential and the yield, but no correlation between the potential and the size, suggesting that the potential relates to stability of oleic acid droplets in water rather than their size. © 2014 The Chemical Society of Japan.

    DOI: 10.1246/cl.131209

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  • Preparation of Magnetic Ionic Liquids Composed of Hybrid-Type Anions Reviewed

    Yumiko Takagi, Yoriko Kusunoki, Yukihiro Yoshida, Hirofusa Tanaka, Gunzi Saito, Kosuke Katagiri, Toshiyuki Oshiki

    AUSTRALIAN JOURNAL OF CHEMISTRY   65 ( 11 )   1557 - 1560   2012

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    1-Ethyl-3-methylimidazolium ethylsulfate ([C(2)mim][EtSO4]) was mixed with iron(III) chloride center dot 6H(2)O to give a magnetic ionic liquid composed of the hybrid-type anion, [C(2)mim][FeCl3 center dot EtSO4], which showed a slightly different magnetic property than [C(2)mim][FeCl4]. On the other hand, reaction of [C(2)mim][EtSO4] with cobalt(II) chloride hydrate formed [C(2)mim](2)[(CoCl4)-Cl-II], the structure of which was characterised by X-ray crystallographic analysis.

    DOI: 10.1071/CH12331

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  • Iridium complexes for the catalytic hydration of acrylonitrile

    Oshiki Toshiyuki, Kawakami Yukiko, Muranaka Makoto

    Proceeding of Annual/Fall Meetings of the Japan Petroleum Institute   2012   133 - 133   2012

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    DOI: 10.11523/sekiyu.2012f.0_133

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  • 2-Diphenylphosphanyl-4-pyridyl(dimethyl) amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions Reviewed

    Makoto Muranaka, Isao Hyodo, Wataru Okumura, Toshiyuki Oshiki

    CATALYSIS TODAY   164 ( 1 )   552 - 555   2011.4

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    New homogeneous catalyst comprised of [Ru(methallyl)(2)(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl) amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 degrees C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of by products. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically. (C) 2010 Elsevier B. V. All rights reserved.

    DOI: 10.1016/j.cattod.2010.11.050

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  • 問われる日本の研究開発力 問われる産と学の決断と勇気

    押木俊之

    化学経済   58 ( 2 )   50-55 - 55   2011.2

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  • Highly Reactive Bifunctional Chemical Catalysts for the Hydration of Nitriles

    Toshiyuki Oshiki, Isao Hyodo, Akinori Ishizuka

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   68 ( 1 )   41 - 51   2010.1

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    New bifunctional chemical catalysts for the hydration of nitriles are described. cis-Ru(acac)(2)(PPh(2)py)(2) exhibited high activity, with a turnover frequency of up to 20,900 (mol of amide)/((mol of catalyst)h). Newly synthesized iridium complexes bearing a PPh(2)py ligand have a 16 e(-) square planar structure. The catalytic hydration of nitriles proceeded at 80 degrees C within few hours to give corresponding amides in almost quantitative yield. Moreover, the iridium complexes acted as a catalyst for the hydration under solvent-free conditions. In addition, new catalysts based on palladium nanoparticles for the hydration are described. Copper compounds containing oxygen atom acted as effective co-catalysts; in the catalytic system.

    DOI: 10.5059/yukigoseikyokaishi.68.41

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  • Tebbe錯体 円偏光二色性検出 2元機能型触媒 非局在型一重項ビラジカル

    高井 和彦, 荒井 孝義, 押木 俊之, 久保 孝史

    有機合成化学協会誌   68 ( 1 )   77 - 77   2010

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    Language:Japanese   Publisher:The Society of Synthetic Organic Chemistry, Japan  

    DOI: 10.5059/yukigoseikyokaishi.68.77

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  • 化学プロセスを見直す加水分解反応の新研究 2元機能型錯体触媒による水和反応

    押木俊之

    月刊ファインケミカル   38 ( 10 )   6-14   2009.9

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  • The Hydration of Nitriles Catalyzed by the Combination of Palladium Nanoparticles and Copper Compounds

    Akinori Ishizuka, Yoshiaki Nakazaki, Toshiyuki Oshiki

    CHEMISTRY LETTERS   38 ( 4 )   360 - 361   2009.4

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    New catalysts based on Pd nanoparticles for the hydration of nitrites to amides were investigated. Copper compounds containing oxygen acted as effective promoters in the catalytic system. The catalysts could be used to prepare aromatic and aliphatic amides from the corresponding nitrites. Chloride ions significantly inhibited the catalytic performance.

    DOI: 10.1246/cl.2009.360

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  • 2元機能型錯体触媒による水和反応

    押木俊之

    月刊ファインケミカル   38 ( 10 )   6 - 11   2009

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  • 環境対応型の加水分解触媒技術(革新的化学触媒を用いるニトリル類の水和(加水分解)技術)

    押木俊之

    クリーンテクノロジー   19   51 - 55   2009

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  • Bio-inspired Highly Active Homogeneous Catalysts for Hydration of Nitriles: Activation of Water under Neutral Conditions

    T. Oshiki, I. Hyodo, M. Muranaka

    J. Biolog. Inorg. Chem.   14(Suppl 1)   S230   2009

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  • 水の資源・エネルギー問題に着目した新規ニトリル水和プロセス

    押木俊之

    グリーンケミストリー研究会資料集   45 - 50   2009

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  • Tantalum Complexes Incorporating Tris(pyrazolyl)Borate Ligands: Syntheses, Structures, and Ethylene Polymerization Behavior

    Michiue, K., Oshiki, T., Takai, K., Mitani, M., Fujita, T.

    Organometallics   28 ( 22 )   6450 - 6457   2009

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    DOI: 10.1021/om9004719

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  • The Hydration of Nitriles Catalyzed by the Combination of Palladium Nanoparticles and Copper Compounds

    Ishizuka, A., Nakazaki, Y., Oshiki, T.

    Chemistry Letters   38 ( 4 )   360-361 (J-STAGE) - 361   2009

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    DOI: 10.1246/cl.2009.360

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  • Efficient Synthesis of Metal Contained Ionic-liquids

    TAKAGI Yumiko, KUSUNOKI Yoriko, OSHIKI Toshiyuki

    香川大学教育学部研究報告 第2部   58 ( 2 )   47-52 - 52   2008.10

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  • INOR 832-Synthesis, structures and olefin polymerization behavior of tris(pyrazolyl)borate tantalum complexes Reviewed

    Kenji Michiue, Toshiyuki Oshiki, Kazuhiko Takai, Makoto Mitani, Terunori Fujita

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   236   2008.8

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  • 高活性錯体触媒法によるアミド製造法の開発

    押木俊之, 石塚章斤, 兵頭功

    ケミカルエンジニアリング   53 ( 6 )   440 - 444   2008

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  • Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors (vol 15, pg 1014, 2007) Reviewed

    Zheng Xiaoxia, Oda Hiroyuki, Takamatsu Kayo, Sugimoto Yukio, Tai Akihiro, Akaho Eiichi, Ali Hamed Ismail, Oshiki Toshiyuki, Kakuta Hiroki, Sasaki Kenji

    BIOORGANIC & MEDICINAL CHEMISTRY   15 ( 9 )   3299 - 3300   2007.5

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    DOI: 10.1016/j.bmc.2007.01.059

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  • Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors Reviewed

    Xiaoxia Zheng, Hiroyuki Oda, Kayo Takamatsu, Yukio Sugimoto, Akihiro Tai, Eiichi Akaho, Hamed Ismail Ali, Toshiyuki Oshiki, Hiroki Kakuta, Kenji Sasaki

    BIOORGANIC & MEDICINAL CHEMISTRY   15 ( 2 )   1014 - 1021   2007.1

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.

    DOI: 10.1016/j.bmc.2006.10.029

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  • Alkyne exchange reactions of silylalkyne complexes of tantalum: Mechanistic investigation and its application in the preparation of new tantalum complexes having functional alkynes (PhC CR (R = COOMe, CONMe2)) Reviewed

    Toshiyuki Oshiki, Atsushi Yamada, Kimio Kawai, Hirotaka Arimitsu, Kazuhiko Takai

    ORGANOMETALLICS   26 ( 1 )   173 - 182   2007.1

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    Silylalkyne complexes of tantalum with the general formula TaCl3((RCCR2)-C-1)L-2 (1, R-1 = R-2 = SiMe3, L-2 = DME; 2, R-1 = SiMe3, R-2 = Me, L-2 = DME; 6, R-1 = R-2 = SiMe3, L = py; 7, R-1 = SiMe3, R-2 = Me, L = py) reacted with an internal alkyne to give corresponding alkyne complexes via an alkyne exchange reaction. These silylalkyne complexes were newly prepared and structurally characterized. Kinetic measurements revealed that the rates of the exchange reactions of the DME complexes 1 and 2 were first-order dependent on the concentration of the complex and the reaction proceeded via dissociative pathway. The exchange reaction rates of the bis(pyridine) complexes 6 and 7 were slower. In contrast to the DME complexes, the exchange reaction of 6 proceeded via an associative interchange pathway, and the exchange mechanism for 7 was an associative pathway. During the exchange, two pyridine ligands coordinated strongly to the tantalum center and the intermediate is proposed to be a bis(alkyne) complex. New tantalum complexes having functional alkynes (PhCCR (R = COOMe, CONMe2)) were prepared from the silylalkyne complexes via the alkyne exchange reaction.

    DOI: 10.1021/om060659z

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  • ニトリル類の水和反応を無溶媒で触媒する新規高活性イリジウム錯体の開発

    触媒   49 ( 6 )   412 - 414   2007

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  • Solvent-free hydration of nitriles catalyzed by homogeneous catalysts

    Oshiki Toshiyuki, Ishizuka Akinori, Okumura Wataru, Hyodo Isao, Arimitsu Hirotaka, Yokoyama Yutaka, Takai Kazuhiko

    Proceeding of Annual/Fall Meetings of the Japan Petroleum Institute   2007   183 - 183   2007

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    We will present that newly discovered pyridylphosphine-ruthenium and -iridium complexes are effective for the catalytic hydration of nitriles. Bifunctional ligand-metal catalysis which was observed in the hydration catalyzed with cis-Ru(acac)2(PPh2py)2 could also play an important role in this reaction. A newly synthesized iridium complex, Ir(acac)(PPh2py)2, proved to be an excellent catalyst for the solvent-free hydration of nitriles. The detailed reaction conditions and molecular structures of the catalysts will also be presented.

    DOI: 10.11523/sekiyu.2007f.0.183.0

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  • Titanium and zirconium complexes with non-salicylaldimine-type imine-phenoxy chelate ligands: Syntheses, structures, and ethylene-polymerization behavior Reviewed

    Suzuki, Y., Tanaka, H., Oshiki, T., Takai, K., Fujita, T.

    Chemistry-an Asian Journal   1 ( 6 )   878-887 - 887   2006.12

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    DOI: 10.1002/asia.200600256

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  • Dramatic rate acceleration by a diphenyl-2-pyridylphosphine ligand in the hydration of nitriles catalyzed by Ru(acac)(2) complexes

    T Oshiki, H Yamashita, K Sawada, M Utsunomiya, K Takahashi, K Takai

    ORGANOMETALLICS   24 ( 26 )   6287 - 6290   2005.12

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    New ruthenium(II) complexes having acac (=acetylacetonato) and diphenyl-2-pyridylphosphine as ligands proved to be excellent catalysts for hydration of nitriles to amides under neutral conditions. Among the ruthenium complexes examined, cis-Ru(acac)(2)(PPh(2)py)(2) exhibited the highest activity, with a turnover frequency of up to 20900 (mol of amide)/((mol of catalyst) h).

    DOI: 10.1021/om050792b

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  • Dramatic rate acceleration by a diphenyl-2-pyridylphosphine ligand in the hydration of nitriles catalyzed by Ru(acac)(2) complexes

    T Oshiki, H Yamashita, K Sawada, M Utsunomiya, K Takahashi, K Takai

    ORGANOMETALLICS   24 ( 26 )   6287 - 6290   2005.12

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    New ruthenium(II) complexes having acac (=acetylacetonato) and diphenyl-2-pyridylphosphine as ligands proved to be excellent catalysts for hydration of nitriles to amides under neutral conditions. Among the ruthenium complexes examined, cis-Ru(acac)(2)(PPh(2)py)(2) exhibited the highest activity, with a turnover frequency of up to 20900 (mol of amide)/((mol of catalyst) h).

    DOI: 10.1021/om050792b

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  • Synthesis of bis(phenoxyimine) Ti alkyl complexes and observation of living species by H-1 NMR spectroscopy

    H Makio, T Oshiki, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1382 - 1383   2005.10

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    Synthesis of [C6F5N=CH(2-O-C6H3-3-R)](2)TiMex (R: Bu-t; X: Br (2), R: Bu-t; X: Me (3), R: H; X: Me (4)) was achieved by the reaction of methylated titanium halides with sodium salts of the phenoxyimine ligands. These complexes can be activated with equimolar amounts of B(C6F5)(3) or Ph3CB(C6F5)(4) to form methyl cationic species, which, upon addition of a small amount of ethylene monomer allows room temperature observation of cationic polymeryl species.

    DOI: 10.1246/cl.2005.1382

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  • Synthesis of bis(phenoxyimine) Ti alkyl complexes and observation of living species by H-1 NMR spectroscopy

    H Makio, T Oshiki, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1382 - 1383   2005.10

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    Synthesis of [C6F5N=CH(2-O-C6H3-3-R)](2)TiMex (R: Bu-t; X: Br (2), R: Bu-t; X: Me (3), R: H; X: Me (4)) was achieved by the reaction of methylated titanium halides with sodium salts of the phenoxyimine ligands. These complexes can be activated with equimolar amounts of B(C6F5)(3) or Ph3CB(C6F5)(4) to form methyl cationic species, which, upon addition of a small amount of ethylene monomer allows room temperature observation of cationic polymeryl species.

    DOI: 10.1246/cl.2005.1382

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  • A novel heteroligated phenoxy-based titanium complex: Structure, stability, and ethylene polymerization behavior

    Y Suzuki, T Oshiki, H Tanaka, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1458 - 1459   2005.10

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    A new phenoxy-imine and phenoxy-ketone heteroligated titanium complex was obtained by hydrolysis of one of the two imine moieties of a bis(phenoxy-imine)Ti complex. X-ray diffraction analysis revealed that the complex assumes an octahedral coordination geometry with a cis-phenoxy-O's and cis-Cl's disposition. NMR studies demonstrated that the complex does not undergo disproportionation. In association with methylaluminoxane, the complex behaved as a non-living-type single-site catalyst for ethylene polymerization.

    DOI: 10.1246/cl.2005.1458

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  • A novel heteroligated phenoxy-based titanium complex: Structure, stability, and ethylene polymerization behavior

    Y Suzuki, T Oshiki, H Tanaka, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1458 - 1459   2005.10

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    A new phenoxy-imine and phenoxy-ketone heteroligated titanium complex was obtained by hydrolysis of one of the two imine moieties of a bis(phenoxy-imine)Ti complex. X-ray diffraction analysis revealed that the complex assumes an octahedral coordination geometry with a cis-phenoxy-O's and cis-Cl's disposition. NMR studies demonstrated that the complex does not undergo disproportionation. In association with methylaluminoxane, the complex behaved as a non-living-type single-site catalyst for ethylene polymerization.

    DOI: 10.1246/cl.2005.1458

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  • Low-temperature catalytic hydrothermal treatment of wood biomass: analysis of liquid products

    S Karagoz, T Bhaskar, A Muto, Y Sakata, T Oshiki, T Kishimoto

    CHEMICAL ENGINEERING JOURNAL   108 ( 1-2 )   127 - 137   2005.4

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    Catalytic hydrothermal treatment of wood biomass was performed at 280° C for 15 min in the presence of alkaline solutions (NaOH, Na2CO3, KOH and K2CO3). Oil products were extracted from both liquid and solid portion by different solvents and analyzed individually. The effect of base solutions on the yield of oil products and composition of oils obtained at different stages were discussed in detail. Based on the conversion and yield of liquid products, the catalytic activity can be ranked as follows: K2CO3 > KOH > Na2CO3 > NaOH. In thermal run, the yield of solid residue was about 42% whereas it was 4.0% in the presence of K2CO3. Catalytic hydrothermal treatment of biomass produced mainly phenolic compounds. In thermal run, furan derivatives were observed whereas these compounds could not be observed in catalytic runs. The volatility distribution of hydrocarbons (ether extract) was characterized by using C-NP gram and it showed that the majority of hydrocarbons for all runs including thermal were distributed boiling point range of n-C-11. The products from hydrothermal treatment of wood biomass were analyzed using GC-MS, H-1 NMR, C-13 NMR, TOC and ion chromatograph. © 2005 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.cej.2005.01.007

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  • Low-temperature catalytic hydrothermal treatment of wood biomass: analysis of liquid products

    S Karagoz, T Bhaskar, A Muto, Y Sakata, T Oshiki, T Kishimoto

    CHEMICAL ENGINEERING JOURNAL   108 ( 1-2 )   127 - 137   2005.4

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    Catalytic hydrothermal treatment of wood biomass was performed at 280° C for 15 min in the presence of alkaline solutions (NaOH, Na2CO3, KOH and K2CO3). Oil products were extracted from both liquid and solid portion by different solvents and analyzed individually. The effect of base solutions on the yield of oil products and composition of oils obtained at different stages were discussed in detail. Based on the conversion and yield of liquid products, the catalytic activity can be ranked as follows: K2CO3 > KOH > Na2CO3 > NaOH. In thermal run, the yield of solid residue was about 42% whereas it was 4.0% in the presence of K2CO3. Catalytic hydrothermal treatment of biomass produced mainly phenolic compounds. In thermal run, furan derivatives were observed whereas these compounds could not be observed in catalytic runs. The volatility distribution of hydrocarbons (ether extract) was characterized by using C-NP gram and it showed that the majority of hydrocarbons for all runs including thermal were distributed boiling point range of n-C-11. The products from hydrothermal treatment of wood biomass were analyzed using GC-MS, H-1 NMR, C-13 NMR, TOC and ion chromatograph. © 2005 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.cej.2005.01.007

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  • Preparation, structural characterization, and reactions of tantalum-alkyne complexes TaCl3((RC)-C-1 CR2)L-2 (L-2 = DME, bipy, and TMEDA; L = Py)

    T Oshiki, K Tanaka, J Yamada, T Ishiyama, Y Kataoka, K Mashima, K Tani, K Takai

    ORGANOMETALLICS   22 ( 3 )   464 - 472   2003.2

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    Tantalum-alkyne complexes with the general formula TaCl3(R(1)CdropCR(2))(dme) (1a, R-1 = R-2 = Et; 1b, R-1 = R-2 = n-C5H11; 1c, R-1 = Ph, R-2 = Me; 1d, R-1 = R-2 = Ph; DME = 1,2-dimethoxyethane) were synthesized by treatment of the corresponding alkynes with a low-valent tantalum derived by reduction of tantalum pentachloride with zinc powder in a mixed solvent of toluene and DME. The DME ligand can be replaced by 2 equiv of pyridine to afford the corresponding dipyridine complexes TaCl3(R(1)CdropCR(2))(py)(2) (2a, R-1 = R-2 = Et; 2b, R-1 = R-2 = n-C5H11; 2c, R-1 = Ph, R-2 = Me; 2d, R-1 = R-2 = Ph). Additionally, the reaction of 1a with the bidentate nitrogen ligands bipyridine and N,N,N',N'-tetramethyethylenediamine (= TMEDA) gave TaCl3(EtCdropCEt)(bipy) (3) and TaCl3(EtCdropCEt)(tmeda) (4), respectively. The eta(2)- and 4e-coordination mode of an alkyne with a large contribution of a metalacyclopropene canonical structure was revealed by spectroscopic methods (NMR and IR) and crystallographic analyses of 1a, 1c, 2a, and 4. The reactivies of the tantalum-3-hexyne complexes la, 2a, 3, and 4 toward 3-phenylpropanal were investigated. Only the pyridine complex 2a reacted with a stoichiometric amount of the aldehyde to afford the corresponding allylic alcohol in 77% yield upon hydrolysis. The reaction proceeded via an oxatantalacyclopentene species.

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  • 新しい均一系クロム錯体触媒によるオレフィン重合

    触媒   43 ( 3 )   235   2001

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  • 錯体触媒によるC-H結合活性化を利用した置換ベンゼン類の新合成法

    Organometallics News   ( 3 )   103   2001

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  • Determination of the absolute configuration of partly fluorinated allylic alcohols; the first synthesis of optically pure 1,2-difluoroallylic alcohols

    Yumiko Takagi, Takiko Nakatani, Toshiyuki Itoh, Toshiyuki Oshiki

    Tetrahedron Letters   41 ( 41 )   7889 - 7892   2000.10

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    Optically active 1,1,2-trifluoro- or 1,2-difluoroallylic alcohols were prepared via a lipase-catalyzed reaction and their absolute configuration was determined by an X-ray crystallographic analysis of the corresponding ferrocene ester along with the refined Mosher method (the Kusumi-Ohtani method). © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01349-6

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  • SYNTHESIS AND REACTIONS OF OPTICALLY-ACTIVE PHOSPHINE-BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, M MATSUO, T HIKOSAKA, M YANAGAWA

    HETEROATOM CHEMISTRY   3 ( 5-6 )   563 - 575   1992.10

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    Synthesis and reactions of optically active phosphine-boranes have been investigated. Optically active secondary phosphine-boranes, (S(p))-and (R(p))-menthyloxyphenylphosphine-boranes, and (S)-methylphenylphosphine-borane underwent palladium(0)-catalyzed electrophilic arylation with o-, m-, or p-iodoanisole. The stereochemistry of this arylation was largely dependent on the solvent and the base used. The reaction in acetonitrile proceeded with almost complete retention of configuration at the chiral phosphorus, whereas inversion of configuration was observed in ethereal solvents or toluene. The phosphorus-oxygen bond of (R(p))-menthyloxy (methyl)phenylphosphine-borane and (S(p))-menthy-loxy(o-methoxyphenyl)phenylphosphine-borane was reductively cleaved at -78-degrees-C by lithium naphthalenide or Li/NH3 with virtually net retention of configuration at phosphorus, providing secondary or tertiary phosphine-boranes in excellent yields. New synthetic routes to optically pure C2-symmetric bisphosphine-boranes possessing chirality at phosphorus have been developed on the basis of these stereochemical studies.

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  • SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, T KUSUMOTO, K SATO

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   112 ( 13 )   5244 - 5252   1990.6

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    DOI: 10.1021/ja00169a036

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  • The Reactions of Optically Pure Menthyloxymethylphenylphosphine-Borane with Organolithium Reagents(共著)

    Toshiyuki Oshiki, Tsuneo Imamoto

    Bulletin of the Chemical Society of Japan   63 ( 12 )   3719 - 3721   1990

  • Synthesis of Organic Phosphorus Compounds Containing a Linear P-B Bond Chain(共著)

    Tetrahedron Letters   30 ( 3 )   383 - 384   1989

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  • 化合物の辞典(共著)

    朝倉書店  1997 

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  • Structural Characterization and Unique Catalytic Performance of Silyl-Group-Substituted Geminal Dichromiomethane Complexes Stabilized with a Diamine Ligand

    Masahito Murai, Ryuji Taniguchi, Naoki Hosokawa, Yusuke Nishida, Hiroko Mimachi, Toshiyuki Oshiki, Kazuhiko Takai

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   139 ( 37 )   13184 - 13192   2017.9

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    Stabilization by a silyl group on the methylene carbon and a diamine ligand led to the isolation of gem-dichromiomethane species. X-ray crystallography confirmed the identity of the structure of this rare example of reactive gem-dimetalloalkane species. The isolated gem-dichromiomethane complex acted as a storable silylmethylidene carbene equivalent, with reactivity that could be changed dramatically upon addition of a Lewis acid (ZnCl2) and a base (TMEDA) to promote both silylalkylidenation of polar aldehydes and silylcyclopropanation of nonpolar alkenes. Identification of a key reactive species also identified the catalytic version of these transformations and provided insights into the reaction mechanism. In contrast to Simmons-Smith cyclopropanation, the real reactive species for the current cyclopropanation was a chromiocarbene species, not a chromium carbenoid species.

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  • Industrial Application and Olefin Metathesis Catalyst Technologies for Reaction Injection Molding of Dicyclopentadiene

    Michiru Kamada, Toshiyuki Oshiki

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   75 ( 2 )   19 - 28   2017.2

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    Current technologies of DCP-RIM (reaction injection molding of dicyclopentadiene) are reviewed from an industrial point of view. The DCP-RIM provides high-impact, heat resistant, and insulating poly (dicyclopentadiene) thermoset resin via catalytic olefin metathesis. Control of chemical reactivities of the catalysts is one of the most important technologies for the DCP-RIM. The key properties of the catalysts are their good solubility in dicyclopentadiene and latency.
    Suitable tungsten or molybdenum-based catalyst systems have been developed and used for over 30 years. These catalyst systems are comprised of inorganic tungsten (or molybdenum) salt and an air-sensitive organoaluminum as an activator. In contrast, robust Grubbs type ruthenium-alkylidene catalysts are attracted great interest in the field of the DCP-RIM. Detailed structure and reactivities of the ruthenium catalysts for the DCP-RIM are summarized.

    DOI: 10.5059/yukigoseikyokaishi.75.111

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  • ジシクロペンタジエンのメタセシス反応による反応射出成形への工業利用と錯体触媒技術

    鎌田満, 押木俊之

    有機合成化学協会誌   75   111 - 120   2017

  • 鉄酸化細菌を用いたAl固溶鞘状酸化鉄の作製

    田村勝徳, 田村勝徳, 久能樹, 久能樹, 長岡紀幸, 中西真, 押木俊之, 高田潤, 高田潤

    セラミックス基礎科学討論会講演要旨集   55th   2017

  • pH Effect on Properties of Surfactant-free Oil-in-water Emulsion Prepared with Oleic Acid

    Yuta Akizuki, Mikio Yoshida, Naoyuki Ishida, Toshiyuki Oshiki, Jun Oshitani

    CHEMISTRY LETTERS   43 ( 5 )   604 - 606   2014.5

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    Size distribution, zeta potential, and yield of surfactant-free oil-in-water (O/W) emulsion prepared with oleic acid were measured at various pHs after seven days from the emulsification. We found that the size distribution is almost the same regardless of pH from 9 to 3. The magnitude of zeta potential and yield remains constant at pH from 9 to 6, and decreases at pH from 6 to 3. There is a correlation between the zeta potential and the yield, but no correlation between the zeta potential and the size, suggesting that the zeta potential relates to stability of oleic acid droplets in water rather than their size.

    DOI: 10.1246/cl.131209

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  • pH Effect on Properties of Surfactant-free Oil-in-water Emulsion Prepared with Oleic Acid

    Yuta Akizuki, Mikio Yoshida, Naoyuki Ishida, Toshiyuki Oshiki, Jun Oshitani

    CHEMISTRY LETTERS   43 ( 5 )   604 - 606   2014.5

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    Size distribution, zeta potential, and yield of surfactant-free oil-in-water (O/W) emulsion prepared with oleic acid were measured at various pHs after seven days from the emulsification. We found that the size distribution is almost the same regardless of pH from 9 to 3. The magnitude of zeta potential and yield remains constant at pH from 9 to 6, and decreases at pH from 6 to 3. There is a correlation between the zeta potential and the yield, but no correlation between the zeta potential and the size, suggesting that the zeta potential relates to stability of oleic acid droplets in water rather than their size.

    DOI: 10.1246/cl.131209

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  • 革新的プロセス開発の新展開 産業界と連携した革新性ある錯体触媒プロセスの開発

    押木俊之

    ケミカルエンジニヤリング   59 ( 2 )   93 - 100   2014

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  • 新用途向けグレードの石油樹脂を提供する新たな触媒技術の開発

    押木俊之, 鎌田満, 西岡直樹

    山陽技術雑誌   61   10 - 14   2014

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  • Attempts of Experimental Class about Ceramics

    48 ( 11 )   889 - 894   2013

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  • Okayama University

    Toshiyuki Oshiki

    ( 3 )   74 - 77   2012

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  • 岡山大学産学官融合センターにおける私の地域産学連携研究

    押木俊之

    ちゅうごく産業創造センター会報   ( 93 )   4 - 7   2012

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  • Preparation of Magnetic Ionic Liquids Composed of Hybrid-Type Anions

    Yumiko Takagi, Yoriko Kusunoki, Yukihiro Yoshida, Hirofusa Tanaka, Gunzi Saito, Kosuke Katagiri, Toshiyuki Oshiki

    AUSTRALIAN JOURNAL OF CHEMISTRY   65 ( 11 )   1557 - 1560   2012

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    1-Ethyl-3-methylimidazolium ethylsulfate ([C(2)mim][EtSO4]) was mixed with iron(III) chloride center dot 6H(2)O to give a magnetic ionic liquid composed of the hybrid-type anion, [C(2)mim][FeCl3 center dot EtSO4], which showed a slightly different magnetic property than [C(2)mim][FeCl4]. On the other hand, reaction of [C(2)mim][EtSO4] with cobalt(II) chloride hydrate formed [C(2)mim](2)[(CoCl4)-Cl-II], the structure of which was characterised by X-ray crystallographic analysis.

    DOI: 10.1071/CH12331

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  • Preparation of Magnetic Ionic Liquids Composed of Hybrid-Type Anions

    Yumiko Takagi, Yoriko Kusunoki, Yukihiro Yoshida, Hirofusa Tanaka, Gunzi Saito, Kosuke Katagiri, Toshiyuki Oshiki

    AUSTRALIAN JOURNAL OF CHEMISTRY   65 ( 11 )   1557 - 1560   2012

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    1-Ethyl-3-methylimidazolium ethylsulfate ([C(2)mim][EtSO4]) was mixed with iron(III) chloride center dot 6H(2)O to give a magnetic ionic liquid composed of the hybrid-type anion, [C(2)mim][FeCl3 center dot EtSO4], which showed a slightly different magnetic property than [C(2)mim][FeCl4]. On the other hand, reaction of [C(2)mim][EtSO4] with cobalt(II) chloride hydrate formed [C(2)mim](2)[(CoCl4)-Cl-II], the structure of which was characterised by X-ray crystallographic analysis.

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  • 2-Diphenylphosphanyl-4-pyridyl(dimethyl) amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

    Makoto Muranaka, Isao Hyodo, Wataru Okumura, Toshiyuki Oshiki

    CATALYSIS TODAY   164 ( 1 )   552 - 555   2011.4

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    New homogeneous catalyst comprised of [Ru(methallyl)(2)(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl) amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 degrees C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of by products. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically. (C) 2010 Elsevier B. V. All rights reserved.

    DOI: 10.1016/j.cattod.2010.11.050

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  • 2-Diphenylphosphanyl-4-pyridyl(dimethyl) amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions

    Makoto Muranaka, Isao Hyodo, Wataru Okumura, Toshiyuki Oshiki

    CATALYSIS TODAY   164 ( 1 )   552 - 555   2011.4

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    New homogeneous catalyst comprised of [Ru(methallyl)(2)(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl) amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 degrees C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of by products. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically. (C) 2010 Elsevier B. V. All rights reserved.

    DOI: 10.1016/j.cattod.2010.11.050

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  • かがやきのあるきらきら光る生き物と触媒

    押木俊之

    羽ばたき   2011

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  • 問われる日本の研究開発力 問われる産と学の決断と勇気

    押木俊之

    化学経済   58 ( 2 )   50 - 55   2011

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  • 産と学の「対話」から生まれた新たな高性能触媒

    押木俊之

    中央会おかやま   ( 7 )   12 - 12   2011

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  • Highly reactive bifunctional chemical catalysts for the hydration of nitriles

    Toshiyuki Oshiki, Isao Hyodo, Akinori Ishizuka

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   68 ( 1 )   41 - 51   2010.1

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    New bifunctional chemical catalysts for the hydration of nitriles are described. cis-Ru(acac)2(PPh2py)2 exhibited high activity, with a turnover frequency of up to 20,900 (mol of amide)/((mol of catalyst)h). Newly synthesized iridium complexes bearing a PPh2py ligand have a 16 e" square planar structure. The catalytic hydration of nitriles proceeded at 80 °C within few hours to give corresponding amides in almost quantitative yield. Moreover, the iridium complexes acted as a catalyst for the hydration under solvent-free conditions. In addition, new catalysts based on palladium nanoparticles for the hydration are described. Copper compounds containing oxygen atom acted as effective co-catalysts in the catalytic system.

    DOI: 10.5059/yukigoseikyokaishi.68.41

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  • 2元機能触媒

    押木俊之

    有機合成化学協会誌   2010

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  • Tantalum Complexes Incorporating Tris(pyrazolyl)Borate Ligands: Syntheses, Structures, and Ethylene Polymerization Behavior

    Kenji Michiue, Toshiyuki Oshiki, Kazuhiko Takai, Makoto Mitani, Terunori Fujita

    ORGANOMETALLICS   28 ( 22 )   6450 - 6457   2009.11

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    Four new Ta complexes bearing tris(pyrazolyl)borate ligands, Tp*TaCl(eta(2)-3-hexyne)(benzyl) [1; Tp* = HB(3,5-dimethylpyrazolyl)(3)(-)], Tp(Ms)*TaCl(2)(eta(2)-3-hexyne) [2; Tp(Ms)* = HB(3-mesitylpyrazolyl)(2)(5-mesitylpyrazolyl)(-)], Tp(Ms)*TaCl(2) (=N-2,6-(i)Pr(2)C(6)H(3)) (3), and Tp(Ms)TaCl(2) (=N-(t)Bu) [4; Tp(Ms) = HB(3-mesitylpyrazolyl)(3)(-)] were prepared in moderate to high yields from appropriate TaCl(3)(R) (R; eta(2)-3-hexyne, =N-2,6-(i)Pr(2)C(6)H(3), =N-(t)Bu) species and the potassium or thallium salt of the corresponding tris(pyrazolyl)borate ligand. The molecular structures of complexes 3 and 4 established by X-ray analyses showed that these complexes adopted a distorted octahedral geometry in which the Ta metal is coordinated by three N atoms of the tris(pyrazolyl)borate ligand (facial coordination), two cis-located Cl atoms, and the imido group. In combination with dried methylaluminoxane or (i)Bu(3)Al/Ph(3)CB(C(6)F(5))(4), complexes 1-4 were all active for ethylene polymerization and produced low to very high molecular weight, highly linear polyethylenes. In particular, upon activation with (i)Bu(3)Al/Ph(3)CB(C(6)F(5))(4), high activities were observed for complexes 3 and 4, which possess the sterically encumbered mesityl-substituted tris(pyrazolyl)borate ligand and the imido group as all auxiliary ligand. The activities, 25.7 kg-PE/mmol-Ta.h (complex 3) and 17.1 kg-PE/mmol-Ta.h (complex 4). represent some of the highest values reported to date for Ta-based catalysts. These highly active Ta-based catalysts were long-lived and maintained a practically steady ethylene uptake for 30 min at 80 degrees C.

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  • Tantalum Complexes Incorporating Tris(pyrazolyl)Borate Ligands: Syntheses, Structures, and Ethylene Polymerization Behavior

    Kenji Michiue, Toshiyuki Oshiki, Kazuhiko Takai, Makoto Mitani, Terunori Fujita

    ORGANOMETALLICS   28 ( 22 )   6450 - 6457   2009.11

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    Four new Ta complexes bearing tris(pyrazolyl)borate ligands, Tp*TaCl(eta(2)-3-hexyne)(benzyl) [1; Tp* = HB(3,5-dimethylpyrazolyl)(3)(-)], Tp(Ms)*TaCl(2)(eta(2)-3-hexyne) [2; Tp(Ms)* = HB(3-mesitylpyrazolyl)(2)(5-mesitylpyrazolyl)(-)], Tp(Ms)*TaCl(2) (=N-2,6-(i)Pr(2)C(6)H(3)) (3), and Tp(Ms)TaCl(2) (=N-(t)Bu) [4; Tp(Ms) = HB(3-mesitylpyrazolyl)(3)(-)] were prepared in moderate to high yields from appropriate TaCl(3)(R) (R; eta(2)-3-hexyne, =N-2,6-(i)Pr(2)C(6)H(3), =N-(t)Bu) species and the potassium or thallium salt of the corresponding tris(pyrazolyl)borate ligand. The molecular structures of complexes 3 and 4 established by X-ray analyses showed that these complexes adopted a distorted octahedral geometry in which the Ta metal is coordinated by three N atoms of the tris(pyrazolyl)borate ligand (facial coordination), two cis-located Cl atoms, and the imido group. In combination with dried methylaluminoxane or (i)Bu(3)Al/Ph(3)CB(C(6)F(5))(4), complexes 1-4 were all active for ethylene polymerization and produced low to very high molecular weight, highly linear polyethylenes. In particular, upon activation with (i)Bu(3)Al/Ph(3)CB(C(6)F(5))(4), high activities were observed for complexes 3 and 4, which possess the sterically encumbered mesityl-substituted tris(pyrazolyl)borate ligand and the imido group as all auxiliary ligand. The activities, 25.7 kg-PE/mmol-Ta.h (complex 3) and 17.1 kg-PE/mmol-Ta.h (complex 4). represent some of the highest values reported to date for Ta-based catalysts. These highly active Ta-based catalysts were long-lived and maintained a practically steady ethylene uptake for 30 min at 80 degrees C.

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  • The Hydration of Nitriles Catalyzed by the Combination of Palladium Nanoparticles and Copper Compounds

    Akinori Ishizuka, Yoshiaki Nakazaki, Toshiyuki Oshiki

    CHEMISTRY LETTERS   38 ( 4 )   360 - 361   2009.4

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    New catalysts based on Pd nanoparticles for the hydration of nitrites to amides were investigated. Copper compounds containing oxygen acted as effective promoters in the catalytic system. The catalysts could be used to prepare aromatic and aliphatic amides from the corresponding nitrites. Chloride ions significantly inhibited the catalytic performance.

    DOI: 10.1246/cl.2009.360

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  • The Hydration of Nitriles Catalyzed by the Combination of Palladium Nanoparticles and Copper Compounds

    Ishizuka, Akinori, Nakazaki Yoshiaki

    Chemistry Letters   38 ( 4 )   360 - 361   2009

  • Bio-inspired highly active homogeneois catalysts for hydration of nitriles: activation of water under neutral conditions

    Toshiyuki Oshiki, Isao Hyodo, Makoto Muranaka

    Journal of Biological Inorganic Chemistry   14   S230-S230   2009

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  • 特集にあたって

    押木俊之

    月刊ファインケミカル   38 ( 10 )   5 - 5   2009

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  • 低炭素社会を先導する革新的化学触媒プロセスの開発

    押木俊之

    岡山大学環境報告書2009   2009

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  • 2元機能型錯体触媒による水和反応

    押木俊之

    月刊ファインケミカル   38 ( 10 )   6 - 14   2009

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  • 環境対応型の加水分解触媒技術 革新的化学触媒を用いるニトリル類の水和(加水分解)技術

    押木俊之

    クリーンテクノロジー   ( 3 )   51 - 54   2009

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  • 高活性錯体触媒法によるアミド製造法の開発

    押木俊之, 石塚章斤, 兵頭功

    ケミカルエンジニヤリング   53 ( 6 )   440 - 444   2008

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  • Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

    Xiaoxia Zheng, Hiroyuki Oda, Kayo Takamatsu, Yukio Sugimoto, Akihiro Tai, Eiichi Akaho, Hamed Ismail Ali, Toshiyuki Oshiki, Hiroki Kakuta, Kenji Sasaki

    BIOORGANIC & MEDICINAL CHEMISTRY   15 ( 2 )   1014 - 1021   2007.1

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    In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.

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  • Alkyne exchange reactions of silylalkyne complexes of tantalum: Mechanistic investigation and its application in the preparation of new tantalum complexes having functional alkynes (PhC CR (R = COOMe, CONMe2))

    Toshiyuki Oshiki, Atsushi Yamada, Kimio Kawai, Hirotaka Arimitsu, Kazuhiko Takai

    ORGANOMETALLICS   26 ( 1 )   173 - 182   2007.1

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    Silylalkyne complexes of tantalum with the general formula TaCl3((RCCR2)-C-1)L-2 (1, R-1 = R-2 = SiMe3, L-2 = DME; 2, R-1 = SiMe3, R-2 = Me, L-2 = DME; 6, R-1 = R-2 = SiMe3, L = py; 7, R-1 = SiMe3, R-2 = Me, L = py) reacted with an internal alkyne to give corresponding alkyne complexes via an alkyne exchange reaction. These silylalkyne complexes were newly prepared and structurally characterized. Kinetic measurements revealed that the rates of the exchange reactions of the DME complexes 1 and 2 were first-order dependent on the concentration of the complex and the reaction proceeded via dissociative pathway. The exchange reaction rates of the bis(pyridine) complexes 6 and 7 were slower. In contrast to the DME complexes, the exchange reaction of 6 proceeded via an associative interchange pathway, and the exchange mechanism for 7 was an associative pathway. During the exchange, two pyridine ligands coordinated strongly to the tantalum center and the intermediate is proposed to be a bis(alkyne) complex. New tantalum complexes having functional alkynes (PhCCR (R = COOMe, CONMe2)) were prepared from the silylalkyne complexes via the alkyne exchange reaction.

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  • ニトリル類の水和反応を無溶媒で触媒する新規高活性イリジウム錯体の開発

    押木俊之, 石塚章斤, 兵頭功, 有光寛高, 高井和彦

    触媒   49 ( 6 )   412 - 414   2007

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  • Titanium and zirconium complexes with non-salicylaldimine-type imine-phenoxy chelate ligands: Syntheses, structures, and ethylene-polymerization behavior

    Yasuhiko Suzuki, Hidetsugu Tanaka, Toshiyuki Oshiki, Kazuhiko Takai, Terunori Fujita

    CHEMISTRY-AN ASIAN JOURNAL   1 ( 6 )   878 - 887   2006.12

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    New Ti and Zr complexes that bear imine-phenoxy chelate ligands, [12,4-di-tBu-6-(RCH=N)C6H40}MCl2] (1: M=Ti, R=Ph; 2: M=Ti, R=C6F5; 3: M=Zr, R=Ph; 4: M=Zr, R=C6F5), were synthesized and investigated as precatalysts for ethylene polymerization. H-1 NMR spectroscopy suggests that these complexes exist as mixtures of structural isomers. X-ray crystallographic analysis of the adduct 1 center dot HCl reveals that it exists as a zwitterionic complex in which H and Cl are situated in close proximity to one of the imine nitrogen atoms and the central metal, respectively. The Xray molecular structure also indicates that one imine phenoxy group with the syn C=N configuration functions as a bidentate ligand, whereas the other, of the anti C=N form, acts as a monodentate phenoxy ligand. Although Zr complexes 3 and 4 with methylaluminoxane (MAO) or [Ph3C](+)[B(C6F5)(4)]/AliBu(3)displayed moderate activity, the Ti congeners 1 and 2, in association with an appropriate activator, catalyzed ethylene polymerization with high efficiency. Upon activation with MAO at 25 degrees C, 2 displayed a very high activity of 19900 (kg PE) (mol Ti)(-1)h(-1), which is comparable to that for [Cp2TiCl2] and [Cp2ZrCl2], although increasing the polymerization temperature did result in a marked decrease in activity. Complex 2 contains a C6F5 group on the imine nitrogen atom and mediated nonliving-type polymerization, unlike the corresponding salicylaldimine-type complex. Conversely, with [Ph3C](-)/[B(C6F5)(4)](-)/AliBu(3) activation, 1 exhibited enhanced activity as the temperature was increased (25-75 degrees C) and maintained very high activity for 60 min at 75 degrees C (18740 (kg PE) (mol Ti)(-1)h(-1)). H-1 NMR spectroscopic studies of the reaction suggest that this thermally robust catalyst system generates an amine-phenoxy complex as the catalytically active species. The combinations 1/[Ph3C](+)[B(C6F5)(4)](-)/AliBu(3) and 2/MAO also worked as high-activity catalysts for the copolymerization of ethylene and propylene.

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  • Dramatic rate acceleration by a diphenyl-2-pyridylphosphine ligand in the hydration of nitriles catalyzed by Ru(acac)(2) complexes

    T Oshiki, H Yamashita, K Sawada, M Utsunomiya, K Takahashi, K Takai

    ORGANOMETALLICS   24 ( 26 )   6287 - 6290   2005.12

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    New ruthenium(II) complexes having acac (=acetylacetonato) and diphenyl-2-pyridylphosphine as ligands proved to be excellent catalysts for hydration of nitriles to amides under neutral conditions. Among the ruthenium complexes examined, cis-Ru(acac)(2)(PPh(2)py)(2) exhibited the highest activity, with a turnover frequency of up to 20900 (mol of amide)/((mol of catalyst) h).

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  • A novel heteroligated phenoxy-based titanium complex: Structure, stability, and ethylene polymerization behavior

    Y Suzuki, T Oshiki, H Tanaka, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1458 - 1459   2005.10

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    A new phenoxy-imine and phenoxy-ketone heteroligated titanium complex was obtained by hydrolysis of one of the two imine moieties of a bis(phenoxy-imine)Ti complex. X-ray diffraction analysis revealed that the complex assumes an octahedral coordination geometry with a cis-phenoxy-O's and cis-Cl's disposition. NMR studies demonstrated that the complex does not undergo disproportionation. In association with methylaluminoxane, the complex behaved as a non-living-type single-site catalyst for ethylene polymerization.

    DOI: 10.1246/cl.2005.1458

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  • Synthesis of bis(phenoxyimine) Ti alkyl complexes and observation of living species by H-1 NMR spectroscopy

    H Makio, T Oshiki, K Takai, T Fujita

    CHEMISTRY LETTERS   34 ( 10 )   1382 - 1383   2005.10

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    Synthesis of [C6F5N=CH(2-O-C6H3-3-R)](2)TiMex (R: Bu-t; X: Br (2), R: Bu-t; X: Me (3), R: H; X: Me (4)) was achieved by the reaction of methylated titanium halides with sodium salts of the phenoxyimine ligands. These complexes can be activated with equimolar amounts of B(C6F5)(3) or Ph3CB(C6F5)(4) to form methyl cationic species, which, upon addition of a small amount of ethylene monomer allows room temperature observation of cationic polymeryl species.

    DOI: 10.1246/cl.2005.1382

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  • Low-temperature catalytic hydrothermal treatment of wood biomass: analysis of liquid products

    S Karagoz, T Bhaskar, A Muto, Y Sakata, T Oshiki, T Kishimoto

    CHEMICAL ENGINEERING JOURNAL   108 ( 1-2 )   127 - 137   2005.4

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    Catalytic hydrothermal treatment of wood biomass was performed at 280° C for 15 min in the presence of alkaline solutions (NaOH, Na2CO3, KOH and K2CO3). Oil products were extracted from both liquid and solid portion by different solvents and analyzed individually. The effect of base solutions on the yield of oil products and composition of oils obtained at different stages were discussed in detail. Based on the conversion and yield of liquid products, the catalytic activity can be ranked as follows: K2CO3 > KOH > Na2CO3 > NaOH. In thermal run, the yield of solid residue was about 42% whereas it was 4.0% in the presence of K2CO3. Catalytic hydrothermal treatment of biomass produced mainly phenolic compounds. In thermal run, furan derivatives were observed whereas these compounds could not be observed in catalytic runs. The volatility distribution of hydrocarbons (ether extract) was characterized by using C-NP gram and it showed that the majority of hydrocarbons for all runs including thermal were distributed boiling point range of n-C-11. The products from hydrothermal treatment of wood biomass were analyzed using GC-MS, H-1 NMR, C-13 NMR, TOC and ion chromatograph. © 2005 Elsevier B.V. All rights reserved.

    DOI: 10.1016/j.cej.2005.01.007

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  • Catalytic performance of tantalum-eta(2)-alkyne complexes [TaCl3((RC)-C-1 CR2)L-2] for alkyne cyclotrimerization

    T Oshiki, H Nomoto, K Tanaka, K Takai

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   77 ( 5 )   1009 - 1011   2004.5

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    Structurally characterized tantalum-eta(2)-alkyne complexes [TaCl3(eta(2)-EtCdropCEt)L-2] (1, L-2 = 1,2-dimethoxyethane (DME); 2, L = py) acted as catalysts for the cyclotrimerization of terminal alkynes. The catalytic reaction proceeded at 25 degreesC within few hours and the trisubstituted benzenes were obtained without the formation of linear oligomers. A new tantalum complex having a terminal alkyne ligand, [TaCl3(eta(2)-Me(3)SiCdropCH)(dme)] (3), was prepared, and its catalytic performance was also investigated.

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  • Preparation, structural characterization, and reactions of tantalum-alkyne complexes TaCl3((RC)-C-1 CR2)L-2 (L-2 = DME, bipy, and TMEDA; L = Py)

    T Oshiki, K Tanaka, J Yamada, T Ishiyama, Y Kataoka, K Mashima, K Tani, K Takai

    ORGANOMETALLICS   22 ( 3 )   464 - 472   2003.2

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    Tantalum-alkyne complexes with the general formula TaCl3(R(1)CdropCR(2))(dme) (1a, R-1 = R-2 = Et; 1b, R-1 = R-2 = n-C5H11; 1c, R-1 = Ph, R-2 = Me; 1d, R-1 = R-2 = Ph; DME = 1,2-dimethoxyethane) were synthesized by treatment of the corresponding alkynes with a low-valent tantalum derived by reduction of tantalum pentachloride with zinc powder in a mixed solvent of toluene and DME. The DME ligand can be replaced by 2 equiv of pyridine to afford the corresponding dipyridine complexes TaCl3(R(1)CdropCR(2))(py)(2) (2a, R-1 = R-2 = Et; 2b, R-1 = R-2 = n-C5H11; 2c, R-1 = Ph, R-2 = Me; 2d, R-1 = R-2 = Ph). Additionally, the reaction of 1a with the bidentate nitrogen ligands bipyridine and N,N,N',N'-tetramethyethylenediamine (= TMEDA) gave TaCl3(EtCdropCEt)(bipy) (3) and TaCl3(EtCdropCEt)(tmeda) (4), respectively. The eta(2)- and 4e-coordination mode of an alkyne with a large contribution of a metalacyclopropene canonical structure was revealed by spectroscopic methods (NMR and IR) and crystallographic analyses of 1a, 1c, 2a, and 4. The reactivies of the tantalum-3-hexyne complexes la, 2a, 3, and 4 toward 3-phenylpropanal were investigated. Only the pyridine complex 2a reacted with a stoichiometric amount of the aldehyde to afford the corresponding allylic alcohol in 77% yield upon hydrolysis. The reaction proceeded via an oxatantalacyclopentene species.

    DOI: 10.1021/om020510x

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  • 私の産学連携への取り組み

    押木俊之

    触媒   45(8), 674   2003

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  • Synthesis and ethylene polymerization behavior of Ti and Zr complexes having imine-phenoxy chelate ligands.

    Y Suzuki, T Oshiki, K Takai, N Kashiwa, T Fujita

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   223   A80 - A81   2002.4

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  • 新しい均一系クロム錯体触媒によるオレフィン重合

    押木俊之

    触媒   第43巻3号235頁   2001

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  • 錯体触媒によるC-H結合活性化を利用した置換ベンゼン類の新合成法

    押木俊之

    Organometallic News   3号, 103頁   2001

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  • Determination of the absolute configuration of partly fluorinated allylic alcohols; the first synthesis of optically pure 1,2-difluoroallylic alcohols

    Yumiko Takagi, Takiko Nakatani, Toshiyuki Itoh, Toshiyuki Oshiki

    Tetrahedron Letters   41 ( 41 )   7889 - 7892   2000.10

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    Optically active 1,1,2-trifluoro- or 1,2-difluoroallylic alcohols were prepared via a lipase-catalyzed reaction and their absolute configuration was determined by an X-ray crystallographic analysis of the corresponding ferrocene ester along with the refined Mosher method (the Kusumi-Ohtani method). © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01349-6

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  • Determination of the absolute configuration of partly fluorinated allylic alcohols; the first synthesis of optically pure 1,2-difluoroallylic alcohols

    Y Takagi, T Nakatani, T Itoh, T Oshiki

    TETRAHEDRON LETTERS   41 ( 41 )   7889 - 7892   2000.10

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    Optically active 1,1,2-trifluoro- or 1,2-difluoroallylic alcohols were prepared via a lipase-catalyzed reaction and their absolute configuration was determined by an X-ray crystallographic analysis of the corresponding ferrocene ester along with the refined Mosher method (the Kusumi-Ohtani method). (C) 2000 Elsevier Science Ltd. All rights reserved.

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  • Determination of the absolute configuration of partly fluorinated allylic alcohols; the first synthesis of optically pure 1,2-difluoroallylic alcohols

    Y Takagi, T Nakatani, T Itoh, T Oshiki

    TETRAHEDRON LETTERS   41 ( 41 )   7889 - 7892   2000.10

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    Optically active 1,1,2-trifluoro- or 1,2-difluoroallylic alcohols were prepared via a lipase-catalyzed reaction and their absolute configuration was determined by an X-ray crystallographic analysis of the corresponding ferrocene ester along with the refined Mosher method (the Kusumi-Ohtani method). (C) 2000 Elsevier Science Ltd. All rights reserved.

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  • Substituent effect on organotin Tp* compounds as the Tp* reagent for the preparation of mono Tp* complexes of group 4-6 metals (Tp* = tris(3,5-dimethylpyrazol-1-yl)hydroborate)

    T Oshiki, K Mashima, S Kawamura, K Tani, K Kitaura

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 8 )   1735 - 1748   2000.8

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    Organotin compounds [Tp* SnCl3-nBun] (2: n = 1; 3: n = 2) having a Tp* ligand(Tp* = tris(3,5-dimethylpyrazol-1-yl)hydroborate) are useful reagents for introducing a Tp* ligand on Group 4 and 5 metals and chromium. The test reactions of these organotin compounds along with [Tp*SnCl3] (1) with ZrCl4, affording a known complex [Tp*ZrCl3] (4), were examined. The reaction rates were in the order 3 > 2 much greater than 1. This tendency was understood by the average Sn-N(Tp* ligand) bond distance being longer in the order 3 > 2 > 1 as revealed by the crystallographic studies and the orbital interactions between the Tp* ligand and the SnCl3-nBun fragments estimated by the ab initio calculations for 1-3. On the basis of the above findings, we applied the compound 3 to prepare Tp* complexes of Group 4-6 metals. Reactions of TiCl4 with an equimolar amount of 3 afforded [Tp*TiCl3] (7) in good yields after a simple rinse to remove the resulting tin compound, SnBu2Cl2. [Tp*HfCl3] (8) was prepared in moderate yield by reaction of [HfCl4(THF)(2)] with 3 under severe conditions. Similarly, the reactions of 3 with a stoichiometric amount of [NbCl4(THF)(2)] or [NbCl5(OEt)(2)] and TaCl5 in toluene gave [Tp*NbCl3] (9) and [Tp*TaCl3][TaCl6] (10), respectively. We also applied our synthetic method to prepare Tp* complexes of vanadium, [Tp*VCl2(THF)] (11), [Tp*VCl2(DNAP)] (12) (DMAP = 4-dimethylaminopyridine), and [Tp*VCl2(=NC6H3Me2-2,6)] (13) and those of chromium, [Tp*CrCl2(L)] (14: L = THF; 15: L = H2O; 16: L = DMAP). Some of these Tp* complexes, 4, 8, 12, 13, 15, and 16 were crystallographically characterized to have discrete octahedral geometry containing the facial coordination of the Tp* ligand.

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  • Substituent effect on organotin Tp* compounds as the Tp* reagent for the preparation of mono Tp* complexes of group 4 - 6 metals (Tp* = tris(3,5-dimethylpyrazol-1-yl)hydroborate)

    Toshiyuki Oshiki, Kazushi Mashima, Shin-Ichi Kawamura, Kazuhide Tani, Kazuo Kitaura

    Bulletin of the Chemical Society of Japan   73 ( 8 )   1735 - 1748   2000.8

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    Organotin compounds [Tp*SnCl3-(n)Bu(n)] (2: n = 1
    3: n = 2) having a Tp* ligand (Tp* = tris(3,5-dimethylpyrazol-1-yl)hydroborate) are useful reagents for introducing a Tp* ligand on Group 4 and 5 metals and chromium. The test reactions of these organotin compounds along with [Tp*SnCl3] (1) with ZrCl4, affording a known complex [Tp*ZrCl3] (4), were examined. The reaction rates were in the order 3 &gt
    2 &gt
    &gt
    1. This tendency was understood by the average Sn-N(Tp* ligand) bond distance being longer in the order 3 &gt
    2 &gt
    1 as revealed by the crystallographic studies and the orbital interactions between the Tp* ligand and the SnCl3-(n)Bu(n) fragments estimated by the ab initio calculations for 1 - 3. On the basis of the above findings, we applied the compound 3 to prepare Tp* complexes of Group 4 - 6 metals. Reactions of TiCl4 with an equimolar amount of 3 afforded [Tp*TiCl3] (7) in good yields after a simple rinse to remove the resulting tin compound, SnBu2Cl2. [Tp*HfCl3] (8) was prepared in moderate yield by reaction of [HfCl4(THF)2] with 3 under severe conditions. Similarly, the reactions of 3 with a stoichiometric amount of [NbCl4(THF)2] or [NbCl5(OEt)2] and TaCl5 in toluene gave [Tp*NbCl3] (9) and [Tp*TaCl3][TaCl6] (10), respectively. We also applied our synthetic method to prepare Tp* complexes of vanadium, [Tp*VCl2(THF)] (11), [Tp*VCl2(DNAP)] (12) (DMAP = 4-dimethylaminopyridine), and [Tp*VCl2(=NC6H3Me2-2,6)] (13) and those of chromium, [Tp*CrCl2(L)] (14: L = THF
    15: L = H2O
    16: L = DMAP). Some of these Tp* complexes, 4, 8, 12, 13, 15, and 16 were crystallographically characterized to have discrete octahedral geometry containing the facial coordination of the Tp* ligand.

    DOI: 10.1246/bcsj.73.1735

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  • Improved synthesis and crystal structure of TiCl3(tmeda)(thf): A highly stereoselective pinacol coupling reagent for aromatic aldehydes

    T Oshiki, T Kiriyama, K Tsuchida, K Takai

    CHEMISTRY LETTERS   ( 4 )   334 - 335   2000.4

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    A monomeric titanium(III) complex, TiCl3(tmeda)(thf) (1), has been prepared by a reaction of TICl4 with TMEDA, Zn, and a catalytic amount of PbCl2 in an almost quantitative yield. The solid state structure of 1 is revealed by X-ray crystallographic analysis. The complex 1 couples aromatic aldehydes under mild conditions to give 1,2-diols in good to excellent yields with high dl-selectivities.

    DOI: 10.1246/cl.2000.334

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  • Improved synthesis and crystal structure of TiCl3(tmeda)(thf): A highly stereoselective pinacol coupling reagent for aromatic aldehydes

    T Oshiki, T Kiriyama, K Tsuchida, K Takai

    CHEMISTRY LETTERS   ( 4 )   334 - 335   2000.4

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    A monomeric titanium(III) complex, TiCl3(tmeda)(thf) (1), has been prepared by a reaction of TICl4 with TMEDA, Zn, and a catalytic amount of PbCl2 in an almost quantitative yield. The solid state structure of 1 is revealed by X-ray crystallographic analysis. The complex 1 couples aromatic aldehydes under mild conditions to give 1,2-diols in good to excellent yields with high dl-selectivities.

    DOI: 10.1246/cl.2000.334

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  • Determination of the Absolute Configuration of Partly Fluorinated Allylic Alcohols"jointly worked"

    Takagi Y, Nakatani T, Itoh T, Oshiki T

    Tetrahedron Letters   41 ( 41 )   7889 - 7892   2000

  • Determination of the Absolute Configuration of Partly Fluorinated Allylic Alcohols

    Takagi Y, Nakatani T, Itoh T, Oshiki T

    Tetrahedron Letters   41 ( 41 )   7889 - 7892   2000

  • Improved synthesis and crystal structure of TiCl3(tmeda)(thf): A highly stereoselective pinacol coupling reagent for aromatic aldehydes

    Toshiyuki Oshiki, Takayuki Kiriyama, Kazuaki Tsuchida, Kazuhiko Takai

    Chemistry Letters   ( 4 )   334 - 335   2000

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    A monomeric titanium(III) complex, TiCl3(tmeda)(thf) (1), has been prepared by a reaction of TiCl4 with TMEDA, Zn, and a catalytic amount of PbCl2 in an almost quantitative yield. The solid state structure of 1 is revealed by X-ray crystallographic analysis. The complex 1 couples aromatic aldehydes under mild conditions to give 1,2-diols in good to excellent yields with high d/-selectivities.

    DOI: 10.1246/cl.2000.334

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  • Substituent Effect on Organotin TP* Compounds as the TP* Reagent for the Preparation of Mono TP* Complexes of Group 4-6 Metals(TP*=Tris(3.5-dimethylpyrazol-1-y<sup>・・・

    Toshiyuki Oshiki, Kazushi Mashima, Kazuhide Tani

    Bulletin of the Chemical Society of Japan   73 ( 8 )   1735 - 1748   2000

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    Substituent Effect on Organotin T&lt;sub&gt;P&lt;/sub&gt;&lt;sup&gt;*&lt;/sup&gt; Compounds as the T&lt;sub&gt;P&lt;/sub&gt;&lt;sup&gt;*&lt;/sup&gt; Reagent for the Preparation of Mono T&lt;sub&gt;P&lt;/sub&gt;&lt;sup&gt;*&lt;/sup&gt; Complexes of Group 4-6 Metals(T&lt;sub&gt;P&lt;/sub&gt;&lt;sup&gt;*&lt;/sup&gt;=Tris(3.5-dimethylpyrazol-1-y&lt;sup&gt;1&lt;/sup&gt;)hydroborate)

    DOI: 10.1246/bcsj.73.1735

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  • Synthesis and Reaction of Samarium(II) Bis(trifluoromethanesulfonate) Derived from Metallic Samarium and 1,5-Dithioniabicyclo[3.3.0]octane Bis(trifluoromethanesulfonate)

    MASHIMA Kazushi, OSHIKI Toshiyuki, TANI Kazuhide

    ( 34 )   186 - 187   1999.5

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  • Synthesis, characterization, and reaction of Samarium(II) bistrifluoromethanesulfonate derived from metallic samarium.

    K Mashima, T Oshiki, K Tani

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   217   U1039 - U1039   1999.3

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  • Oxidative addition of a hypervalent transannular sulfur-sulfur bond to a Pd(0) complex: Synthesis and crystal structures of 1,5-Dithiacyclooctanepalladium(II)bis(trifluoromethanesulfonate) having phosphine ligands

    T Oshiki, K Mashima, T Yamagata, K Tani

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   71 ( 12 )   2859 - 2864   1998.12

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    A hypervalent compound 1,5-bis(trifluoromethylsulfonyloxy)-1 lambda(4),5 lambda(4)-dithiabicyclo[3.3.0]octane (1) oxidatively reacted with Pd-2(dba)(3) (dba = dibenzylidene acetone) in acetonitrile to give a dicationic complex [Pd(dtco)(CH3CN)(2)](OTf)(2) (2) (DTCO = 1,5-dithiacyclooctane), in which the DTCO ligand coordinated in cis-chelation to the palladium metal. Acetonitrile in 2 was labile enough to be readily replaced by phosphine ligands to give dicationic DTCO-phosphine palladium complexes of the formula [Pd(dtco)(L)(2)](OTf)(2) (3: L = PMe2Ph; 4: L = PPh3; 5. L-2 = 1,2-bis(diphenylphosphino)ethane; 6: L-2 = (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl). Molecular structures of 5 and 6 have been characterized by X-ray analysis, indicating that each of these two complexes consists of a discrete dicationic palladium(II) species [Pd(dtco)L-2](2+) and two trifluoromethanesulfonate ions without any cation-anion bonding interaction, and revealing that the DTCO is coordinated to the palladium center as a bidentate ligand and that two phosphorus atoms ultimately coordinated to the metal in cis-fashion.

    DOI: 10.1246/bcsj.71.2859

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  • Isolation and reactions of a tantalum-imine complex TaCl3(dme)(PhCH=NCH2Ph)

    K Takai, T Ishiyama, H Yasue, T Nobunaka, M Itoh, T Oshiki, K Mashima, K Tani

    ORGANOMETALLICS   17 ( 23 )   5128 - 5132   1998.11

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    A new tantalum-imine complex TaCl3(dme)(PhCH=NCH2Ph) (1) (DME = 1,2-dimethoxy-ethane) was synthesized by treatment of N-(benzylidene)benzylamine with low-valent tantalum derived from TaCl5 and zinc in DME and toluene. The molecular structure of complex 1 was determined by X-ray crystallographic analysis, and its reactivity toward unsaturated compounds examined.

    DOI: 10.1021/om980380l

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  • Isolation and reactions of a tantalum-imine complex TaCl3(dme)(PhCH=NCH2Ph)

    K Takai, T Ishiyama, H Yasue, T Nobunaka, M Itoh, T Oshiki, K Mashima, K Tani

    ORGANOMETALLICS   17 ( 23 )   5128 - 5132   1998.11

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    A new tantalum-imine complex TaCl3(dme)(PhCH=NCH2Ph) (1) (DME = 1,2-dimethoxy-ethane) was synthesized by treatment of N-(benzylidene)benzylamine with low-valent tantalum derived from TaCl5 and zinc in DME and toluene. The molecular structure of complex 1 was determined by X-ray crystallographic analysis, and its reactivity toward unsaturated compounds examined.

    DOI: 10.1021/om980380l

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  • Dialkylchromium complexes bearing a hydrotris(3,5-dimethylpyrazolyl)borate ligand: synthesis and crystal structures of Tp*CrMe2(DMAP) and Tp*Cr(Cr(CH2Ph)(2)(DMAP) (DMAP = 4-dimethylaminopyridine)

    K Mashima, T Oshiki, K Tani, T Aoshima, H Urata

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   569 ( 1-2 )   15 - 19   1998.10

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    The synthesis and the crystallographic characterization of two dialkylchromium complexes possessing a Tp* ligand, i.e. Tp*CrMe2(DMAP) (4) and Tp*Cr(CH2Ph)(2)(DMAP) (5) (Tp* =hydrotris(3,5-dimethylpyrazolyl)borate; DMAP=4-dimethylaminopyridine), are described. Treatment of Tp*CrCl2(DMAP) (3) with two equivalents of MeLi gave 4, while the complex 5 was prepared by the reaction of 3 with two equivalents of PhCH2MgCl. These complexes were found to be thermally robust and quite stable to air and moisture. Distorted octahedral geometry around each chromium center of 4 and 5 has been determined by X-ray analysis, the chromium center being surrounded with three nitrogen atoms of the Tp* ligand at facial positions, one nitrogen atom of the DMAP ligand, and two carbon atoms. The two benzyl ligands of 5 were found to coordinate to the chromium center in eta(1)-fashion. (C) 1998 Elsevier Science S.A. All rights reserved.

    DOI: 10.1016/S0022-328X(98)00769-4

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  • The first oxidative addition of a hypervalent compound to metallic lanthanoid: Synthesis, characterization, and reaction of samarium(II) bis(trifluoromethanesulfonate) derived from metallic samarium and 1,5-dithioniabicyclo[3.3.0]octane bis(trifluoromethanesulfonate)

    K Mashima, T Oshiki, K Tani

    JOURNAL OF ORGANIC CHEMISTRY   63 ( 20 )   7114 - 7116   1998.10

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    DOI: 10.1021/jo981436o

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  • The first oxidative addition of a hypervalent compound to metallic lanthanoid: Synthesis, characterization, and reaction of samarium(II) bis(trifluoromethanesulfonate) derived from metallic samarium and 1,5-dithioniabicyclo[3.3.0]octane bis(trifluoromethanesulfonate)

    K Mashima, T Oshiki, K Tani

    JOURNAL OF ORGANIC CHEMISTRY   63 ( 20 )   7114 - 7116   1998.10

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    The First Oxidative Addition of a Hypervalent Compound to Metallic Lanthanoid : Synthesis, Characterization, and Reaction of Samarium((]G0002[))Bis(trifluoromethanesulfonate)Derived from Metallic Samarium and 1,5-Dithioniabicyclo[3.3.0]octane Bis(trifluoromethanesulfonate)&quot;jointly worked&quot;

    DOI: 10.1021/jo981436o

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  • Oxidative Addition of a Hypervalent Transannular Sulfur-Sulfur Bond to a Pd(0)Complex : Synthesis and Crystal Structure of 1,5-Dithioniabicyclooctanepalladium((]G0002[))Bis(trifluoromethanesulfonate) Having Phosphine Ligands"jointly worked"

    Oshiki T, Mashima K, Yamagata T, Tani K

    Bulletin of the Chemical Society of Japan   71 ( 12 )   2859 - 2864   1998

  • Dialkylchromium Complexes bearing a Hydrotris(3,5-dimethylpyrazolyl)borate Ligand : Synthesis and Crystal Structures of Tp*CrMe2(DMAP)and Tp*Cr(CH2Ph)2(DMAP)(DMAP=4 dimethylaminopyridine)"jointly w・・・

    Mashima K, Oshiki T, Tani K, Aoshima T, Urata H

    Journal of Organometallic Chemistry   569 ( 1-2 )   15 - 19   1998

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    Dialkylchromium Complexes bearing a Hydrotris(3,5-dimethylpyrazolyl)borate Ligand : Synthesis and Crystal Structures of Tp&lt;sup&gt;*&lt;/sup&gt;CrMe&lt;sup&gt;2&lt;/sup&gt;(DMAP)and Tp&lt;sup&gt;*&lt;/sup&gt;Cr(CH&lt;sup&gt;2&lt;/sup&gt;Ph)&lt;sup&gt;2&lt;/sup&gt;(DMAP)(DMAP=4 dimethylaminopyridine)&quot;jointly worked&quot;

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  • Tp*Sn(Cl)Bu-2 as a convenient reagent for the preparation of hydrotris(3,5-dimethylpyrazolyl)borate complexes of niobium, tantalum, and zirconium

    K Mashima, T Oshiki, K Tani

    ORGANOMETALLICS   16 ( 13 )   2760 - 2762   1997.6

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    Organotin complexes bearing a Tp* ligand, Tp*Sn(Cl)(n)Bu3-n (1, n = 1; 2, n = 2; Tp* = hydrotris-(3,5-dimethylpyrazolyl)borate), were found to be useful reagents for introducing a Tp* ligand on niobium and tantalum as well as zirconium. The reactivities of these organotin compounds together with Tp*SnCl3 (3) were compared directly by using the reaction with ZrCl4, which affords Tp*ZrCl3(4), as a test case. The reaction rate was in the order 1 &gt; 2 much greater than 3. Thus, complex 1 was used for the preparation of Tp*NbCl3 (5) and [Tp*TaCl3]-[TaCl6] (6), whose structures mere confirmed by X-ray analysis. X-ray analysis of 1 indicated that one of the three Sn-N bonds in 1 was cleaved and that the Sn atom adopted a five-coordinate square pyramidal geometry that made complex 1 more reactive than the six-coordinate complexes 2 and 3.

    DOI: 10.1021/om9701175

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  • Synthesis and Structure of Lanthanoid Complexes Derived From Reactions of Metallic Lanthanoids with Azobenzene and Cyclooctatetraene

    MASHIMA K., FUKUMOTO H., OSHIKI T., TANI K., NAKAYAMA Y., NAKAMURA A.

    ( 30 )   96 - 97   1997.5

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  • Oxidative Reaction of 1,5-Dithioniabicyclo[3.3.0]octane Bis(trifluoromethanesulfonate) with Diene Complexes of Zirconium and Tantalum : Rational Preparation of Cp2Zr(COf)2(thf)and Cp(η4-1,3 butadiene)Ta(OTf)2・・・

    Mashima K, Oshiki T, Matsuo Y, Tani K

    Chemistry Letters   ( 8 )   793 - 794   1997

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    Oxidative Reaction of 1,5-Dithioniabicyclo[3.3.0]octane Bis(trifluoromethanesulfonate) with Diene Complexes of Zirconium and Tantalum : Rational Preparation of Cp&lt;sub&gt;2&lt;/sub&gt;Zr(COf)&lt;sub&gt;2&lt;/sub&gt;(thf)and Cp(η&lt;sup&gt;4&lt;/sup&gt;-1,3 butadiene)Ta(OTf)&lt;sub&gt;2&lt;/sub&gt;&quot;jointly worked&quot;

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  • Tp*Sn(Cl)Bu2 as a Convenient Reagent for the Preparation of Hydrotris(3,5-Dimethylpyrazolyl)borate Complexes of Niobium, Tantalum, and Zirconium"jointly worked"

    Mashima K, Oshiki T, Tani K

    Organometallics   16 ( 13 )   2760 - 2762   1997

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  • Oxidative reaction of 1,5-dithioniabicyclo[3.3.0]octane bis(trifluoromethanesulfonate) with diene complexes of zirconium and tantalum: Synthesis of Cp2Zr(OTf)(2)(thf) and Cp(eta(4)-1,3-butadiene)Ta(OTf)(2)

    K Mashima, T Oshiki, Y Matsuo, K Tani

    CHEMISTRY LETTERS   ( 8 )   793 - 794   1997

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    Oxidative addition of a hypervalent organosulfur compound, 1,5-dithioniabicyclo[3.3.0]octane bis(trifluoromethanesulfonate) (1), to diene complexes of zirconium and tantalum, Cp2Zr(eta(4)-1,3-butadiene) and CpTa(eta(4)-1,3-butadiene)(2), in THF resulted in the almost quantitative formation of bis(triflate) complexes of zirconium, Cp2Zr(OTf)(2)(thf) (3), and tantalum, CpTa(eta(4)-1,3-butadiene)(OTf)(2) (5), respectively.

    DOI: 10.1246/cl.1997.793

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  • LIVING POLYMERIZATION OF ETHYLENE CATALYZED BY DIENE COMPLEXES OF NIOBIUM AND TANTALUM, M(ETA(5)-C(5)ME(5))(ETA(4)-DIENE)X(2) AND M(ETA(5)-C(5)ME(5))(ETA(4)-DIENE)(2)(M= NB AND TA), IN THE PRESENCE OF METHYLALUMINOXANE

    K MASHIMA, S FUJIKAWA, Y TANAKA, H URATA, T OSHIKI, E TANAKA, A NAKAMURA

    ORGANOMETALLICS   14 ( 6 )   2633 - 2640   1995.6

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    Catalyst systems of MX(2)(eta(5)-C(5)R(5))(eta(4)-diene) (M = Nb and Ta; R = H and CH3; X = Cl and CH3) in a combination of methylaluminoxane (MAO) are the precursors of the living polymerization of ethylene. Mono-diene complexes MCl(2)(eta(5)-C(5)R(5))(eta(4)-diene) [M = Nb, R = CH3 (1); M = Ta, R = CHS (2); M = Ta, R = H (3); M = Nb, R = H (4); diene = buta-1,3-diene (a), isoprene (b), 2,3-dimethylbuta-1,3-diene (c)] were prepared by the reaction of MCl(4)(eta(5)-C(5)R(5)) with 2 equiv of the methylated allyl Grignard reagents in THF. Reaction of 2 and 3 with MeMgI afforded dimethyl complexes, Ta(eta(5)-C(5)R(5))(eta(4)-1,3-butadiene)Me(2) [R = CH3 (5); R = H (6)], respectively. The polymerization of ethylene catalyzed by 1/MAO, 2/MAO, and 5/MAO at low temperature (-20 degrees C) gave polyethylene with very narrow polydispersities (M(w)/M(n) as low as 1.05). The niobium complexes are superior to the tantalum complexes in terms of the catalyst activity and the polydispersity. When the ligand was Cp instead of Cp*, the catalyst activity of 3 for the polymerization of ethylene at -20 degrees C increased but the polydispersity of the obtained polyethylene broadened (M(w)/M(n) = 1.40). Protolytic reaction of 5b with 1 equiv of TfOH produces TaCp*(eta 4-isoprene)(CH3)(OSO2CF3) (7), whose structure is determined by single-crystal X-ray diffractometry. Compound 7 crystallizes in the orthorhombic space group P2(1)2(1)2(1) (No. 19) with a = 13.388(6) Angstrom, b = 16.196(4) Angstrom, c = 9.214(4) Angstrom, Z = 4, V = 1998(1) Angstrom(3), D-calcd = 1.823 g/mL, and R = 0.041 based on 2191 reflections. The molecular structure shows that 7 is not a cationic complex. The tantalum atom is in a chiral center surrounded by four different ligands: eta(1)-triflate, eta(5)-Cp*, eta(4)-isoprene, and methyl. A cationic species derived from 5b and B(C6F5)(3) was detected by H-1 NMR spectroscopy and found to be active in ethylene polymerization. A system of one of the bis-diene complexes of the type M(eta 5-C(5)R(5))(eta(4)-2,3-dimethyl-1,3-butadiene)(2) [M = Nb, R = H (8); M = Nb, R = CH3 (9); M = Ta, R = CH3 (10)] in the presence of a large excess of MAO was also found to be an active catalyst for the polymerization of ethylene.

    DOI: 10.1021/om00006a008

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  • LIVING POLYMERIZATION OF ETHYLENE CATALYZED BY DIENE COMPLEXES OF NIOBIUM AND TANTALUM, M(ETA(5)-C(5)ME(5))(ETA(4)-DIENE)X(2) AND M(ETA(5)-C(5)ME(5))(ETA(4)-DIENE)(2)(M= NB AND TA), IN THE PRESENCE OF METHYLALUMINOXANE

    K MASHIMA, S FUJIKAWA, Y TANAKA, H URATA, T OSHIKI, E TANAKA, A NAKAMURA

    ORGANOMETALLICS   14 ( 6 )   2633 - 2640   1995.6

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    Catalyst systems of MX(2)(eta(5)-C(5)R(5))(eta(4)-diene) (M = Nb and Ta; R = H and CH3; X = Cl and CH3) in a combination of methylaluminoxane (MAO) are the precursors of the living polymerization of ethylene. Mono-diene complexes MCl(2)(eta(5)-C(5)R(5))(eta(4)-diene) [M = Nb, R = CH3 (1); M = Ta, R = CHS (2); M = Ta, R = H (3); M = Nb, R = H (4); diene = buta-1,3-diene (a), isoprene (b), 2,3-dimethylbuta-1,3-diene (c)] were prepared by the reaction of MCl(4)(eta(5)-C(5)R(5)) with 2 equiv of the methylated allyl Grignard reagents in THF. Reaction of 2 and 3 with MeMgI afforded dimethyl complexes, Ta(eta(5)-C(5)R(5))(eta(4)-1,3-butadiene)Me(2) [R = CH3 (5); R = H (6)], respectively. The polymerization of ethylene catalyzed by 1/MAO, 2/MAO, and 5/MAO at low temperature (-20 degrees C) gave polyethylene with very narrow polydispersities (M(w)/M(n) as low as 1.05). The niobium complexes are superior to the tantalum complexes in terms of the catalyst activity and the polydispersity. When the ligand was Cp instead of Cp*, the catalyst activity of 3 for the polymerization of ethylene at -20 degrees C increased but the polydispersity of the obtained polyethylene broadened (M(w)/M(n) = 1.40). Protolytic reaction of 5b with 1 equiv of TfOH produces TaCp*(eta 4-isoprene)(CH3)(OSO2CF3) (7), whose structure is determined by single-crystal X-ray diffractometry. Compound 7 crystallizes in the orthorhombic space group P2(1)2(1)2(1) (No. 19) with a = 13.388(6) Angstrom, b = 16.196(4) Angstrom, c = 9.214(4) Angstrom, Z = 4, V = 1998(1) Angstrom(3), D-calcd = 1.823 g/mL, and R = 0.041 based on 2191 reflections. The molecular structure shows that 7 is not a cationic complex. The tantalum atom is in a chiral center surrounded by four different ligands: eta(1)-triflate, eta(5)-Cp*, eta(4)-isoprene, and methyl. A cationic species derived from 5b and B(C6F5)(3) was detected by H-1 NMR spectroscopy and found to be active in ethylene polymerization. A system of one of the bis-diene complexes of the type M(eta 5-C(5)R(5))(eta(4)-2,3-dimethyl-1,3-butadiene)(2) [M = Nb, R = H (8); M = Nb, R = CH3 (9); M = Ta, R = CH3 (10)] in the presence of a large excess of MAO was also found to be an active catalyst for the polymerization of ethylene.

    DOI: 10.1021/om00006a008

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  • SYNTHESIS AND REACTIONS OF OPTICALLY-ACTIVE PHOSPHINE-BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, M MATSUO, T HIKOSAKA, M YANAGAWA

    HETEROATOM CHEMISTRY   3 ( 5-6 )   563 - 575   1992.10

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    Synthesis and reactions of optically active phosphine-boranes have been investigated. Optically active secondary phosphine-boranes, (S(p))-and (R(p))-menthyloxyphenylphosphine-boranes, and (S)-methylphenylphosphine-borane underwent palladium(0)-catalyzed electrophilic arylation with o-, m-, or p-iodoanisole. The stereochemistry of this arylation was largely dependent on the solvent and the base used. The reaction in acetonitrile proceeded with almost complete retention of configuration at the chiral phosphorus, whereas inversion of configuration was observed in ethereal solvents or toluene. The phosphorus-oxygen bond of (R(p))-menthyloxy (methyl)phenylphosphine-borane and (S(p))-menthy-loxy(o-methoxyphenyl)phenylphosphine-borane was reductively cleaved at -78-degrees-C by lithium naphthalenide or Li/NH3 with virtually net retention of configuration at phosphorus, providing secondary or tertiary phosphine-boranes in excellent yields. New synthetic routes to optically pure C2-symmetric bisphosphine-boranes possessing chirality at phosphorus have been developed on the basis of these stereochemical studies.

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  • SYNTHESIS AND REACTIONS OF OPTICALLY-ACTIVE PHOSPHINE-BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, M MATSUO, T HIKOSAKA, M YANAGAWA

    HETEROATOM CHEMISTRY   3 ( 5-6 )   563 - 575   1992.10

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    Synthesis and reactions of optically active phosphine-boranes have been investigated. Optically active secondary phosphine-boranes, (S(p))-and (R(p))-menthyloxyphenylphosphine-boranes, and (S)-methylphenylphosphine-borane underwent palladium(0)-catalyzed electrophilic arylation with o-, m-, or p-iodoanisole. The stereochemistry of this arylation was largely dependent on the solvent and the base used. The reaction in acetonitrile proceeded with almost complete retention of configuration at the chiral phosphorus, whereas inversion of configuration was observed in ethereal solvents or toluene. The phosphorus-oxygen bond of (R(p))-menthyloxy (methyl)phenylphosphine-borane and (S(p))-menthy-loxy(o-methoxyphenyl)phenylphosphine-borane was reductively cleaved at -78-degrees-C by lithium naphthalenide or Li/NH3 with virtually net retention of configuration at phosphorus, providing secondary or tertiary phosphine-boranes in excellent yields. New synthetic routes to optically pure C2-symmetric bisphosphine-boranes possessing chirality at phosphorus have been developed on the basis of these stereochemical studies.

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  • UNPRECEDENTED STEREOCHEMISTRY OF THE ELECTROPHILIC ARYLATION AT CHIRAL PHOSPHORUS

    T OSHIKI, T IMAMOTO

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   114 ( 10 )   3975 - 3977   1992.5

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    DOI: 10.1021/ja00036a054

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  • Unprecedented Stereochemistry of the Electrophilic Arylation at Chiral Phosphorus"jointly worked"

    OSHIKI T, IMAMOTO T

    Journal of the American Chemical Society   114 ( 10 )   3975 - 3977   1992

  • STEREOSPECIFIC REDUCTION OF MENTHYLOXYPHOSPHINE-BORANES WITH ONE-ELECTRON REDUCING AGENTS

    T OSHIKI, T HIKOSAKA, T IMAMOTO

    TETRAHEDRON LETTERS   32 ( 28 )   3371 - 3374   1991.7

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    The phosphorus-oxygen bond of diastereomerically pure methyloxyphosphine-boranes was reductively cleaved at -78-degrees-C by lithium naphthalenide or Li-NH3 in excellent yields with almost complete retention of configuration at phosphorus.

    DOI: 10.1016/S0040-4039(00)92709-6

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  • STEREOSPECIFIC REDUCTION OF MENTHYLOXYPHOSPHINE-BORANES WITH ONE-ELECTRON REDUCING AGENTS

    T OSHIKI, T HIKOSAKA, T IMAMOTO

    TETRAHEDRON LETTERS   32 ( 28 )   3371 - 3374   1991.7

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    The phosphorus-oxygen bond of diastereomerically pure methyloxyphosphine-boranes was reductively cleaved at -78-degrees-C by lithium naphthalenide or Li-NH3 in excellent yields with almost complete retention of configuration at phosphorus.

    DOI: 10.1016/S0040-4039(00)92709-6

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  • THE REACTIONS OF OPTICALLY PURE METHYLOXYMETHYLPHENYLPHOSPHINE-BORANE WITH ORGANOLITHIUM REAGENTS

    T OSHIKI, T IMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   63 ( 12 )   3719 - 3721   1990.12

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    The reactions of (R(p))-methyloxymethyl-phenylphosphine-borane with several organolithium reagents are described. Less sterically hindered reagents such as m-anisyllithium and p-anisyllithium react with the phosphine-borane to afford the corresponding substitution products with high stereochemical integrity with inversion of configuration. On the other hand, omicron-substituted phenyllithiums lead to products possessing very low optical purities.

    DOI: 10.1246/bcsj.63.3719

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  • THE REACTIONS OF OPTICALLY PURE METHYLOXYMETHYLPHENYLPHOSPHINE-BORANE WITH ORGANOLITHIUM REAGENTS

    T OSHIKI, T IMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   63 ( 12 )   3719 - 3721   1990.12

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    The reactions of (R(p))-methyloxymethyl-phenylphosphine-borane with several organolithium reagents are described. Less sterically hindered reagents such as m-anisyllithium and p-anisyllithium react with the phosphine-borane to afford the corresponding substitution products with high stereochemical integrity with inversion of configuration. On the other hand, omicron-substituted phenyllithiums lead to products possessing very low optical purities.

    DOI: 10.1246/bcsj.63.3719

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  • SYNTHESIS AND REACTIONS OF PHOSPHINE-METHYLSULFONYLOXYBORANE COMPLEXES

    T OSHIKI, T IMAMOTO

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   63 ( 10 )   2846 - 2849   1990.10

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    DOI: 10.1246/bcsj.63.2846

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  • SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, T KUSUMOTO, K SATO

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   112 ( 13 )   5244 - 5252   1990.6

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    DOI: 10.1021/ja00169a036

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  • SYNTHESIS AND REACTIONS OF PHOSPHINE BORANES - SYNTHESIS OF NEW BIDENTATE LIGANDS WITH HOMOCHIRAL PHOSPHINE CENTERS VIA OPTICALLY PURE PHOSPHINE BORANES

    T IMAMOTO, T OSHIKI, T ONOZAWA, T KUSUMOTO, K SATO

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   112 ( 13 )   5244 - 5252   1990.6

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    DOI: 10.1021/ja00169a036

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  • Synthesis and reactions of phosphine-methylsulfonyloxyborane complexes

    Toshiyuki Oshiki, Tsuneo Imamoto

    Bulletin of the Chemical Society of Japan   63 ( 10 )   2846 - 2849   1990

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    Functionalizations of the boranato group of phosphine-boranes have been investigated. Trimethylphosphine-borane readily reacted with methanesulfonic acid in dichloromethane with evolution of hydrogen. The resulting trimethylphosphine-methylsulfonyloxyborane was subjected to nucleophilic substitution reaction on the boron atom with arenethiols or secondary phosphine-boranes in the presence of NaH. The reactivities of the substitution products obtained were also investigated. A new phosphine-borane having a P-B-P-B-P-BP-B bond linkage was synthesized. © 1990 The Chemical Society of Japan.

    DOI: 10.1246/bcsj.63.2846

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  • SYNTHESIS OF ORGANIC PHOSPHORUS-COMPOUNDS CONTAINING A LINEAR P-B BOND CHAIN

    T IMAMOTO, T OSHIKI

    TETRAHEDRON LETTERS   30 ( 3 )   383 - 384   1989

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    DOI: 10.1016/S0040-4039(00)95208-0

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  • SYNTHESIS OF ORGANIC PHOSPHORUS-COMPOUNDS CONTAINING A LINEAR P-B BOND CHAIN

    T IMAMOTO, T OSHIKI

    TETRAHEDRON LETTERS   30 ( 3 )   383 - 384   1989

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    DOI: 10.1016/S0040-4039(00)95208-0

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Presentations

  • タングステン錯体触媒系によるジシクロペンタジエンの重合

    押木俊之

    第72回高分子討論会  2023.9.26 

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    Event date: 2023.9.26 - 2023.9.28

    Language:Japanese   Presentation type:Poster presentation  

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  • New Homogeneous Tungsten Catalysts for Bulk Metathesis Polymerization of Cycloolefins

    Toshiyuki Oshiki

    The 13th SPSJ International Polymer Conference  2023.7.19 

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    Event date: 2023.7.18 - 2023.7.21

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  • シクロオレフィンのバルク重合に適するタングステン系錯体触媒

    押木俊之, 永井大登, 佐野航介

    第72回高分子学会年次大会  2023.5.24 

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    Event date: 2023.5.24 - 2023.5.26

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  • 二次元ナノシート強化樹脂の開発 Invited

    仁科勇太, 押木俊之, 中西真, 中野知佑

    令和4年度大学等シーズ発信会  2023.3.15 

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    Event date: 2023.3.15

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  • 開環メタセシス重合用錯体触媒となる タングステン前駆体の183W NMRによる分析

    押木俊之, 永井大登, 佐野航介, 越野広雪, 小松功典, 武藤仁美

    長野大会(第52回石油・石油化学討論会)  2022.10.28 

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    Event date: 2022.10.27 - 2022.10.28

    Language:Japanese   Presentation type:Oral presentation (general)  

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  • オープンイノベーション機構設置研究会・岡山大学

    Toshiyuki Oshiki

    nanotech2019 

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    Event date: 2019.1.31 - 2019.2.1

    Language:Japanese   Presentation type:Poster presentation  

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  • MADE IN JAPAN Invited

    Toshiyuki Oshiki

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    Event date: 2018.8.30 - 2018.8.31

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  • 多核を含めた溶液NMRの古くて新しい測定手法 Invited

    押木俊之

    第1回分子研NMRセミナー  2022.11.14 

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    Language:Japanese   Presentation type:Oral presentation (invited, special)  

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  • 分離操作不要のメタセシス重合用新規タングステン錯体触媒の合成

    永井大登, 押木俊之

    2020.6.29 

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  • キレート型モノアニオン配位子を用いる新しい重合用錯体触媒の合成

    2020.5.24 

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  • 開環メタセシス重合の触媒前駆体となる置換フェノキシ基をもつタングステン錯体の合成経路

    2019.11.1 

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  • オープンイノベーション機構を目指した岡山大学の材料開発技術紹介

    2019.1.31 

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  • オレフィンメタセシスを起こすタングステン錯体の分子構造

    第121回触媒討論会  2018 

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  • 均質な粒ぞろいの新材料が産み出す革新素材

    岡山大学 知恵の見本市 2017  2017 

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  • 1,3-ジケトンの配位したオキソタングステン錯体とフェノール類の反応により生成する錯体の分子構造とメタセシス触媒機能

    鳥取大会(第47回石油・石油化学討論会)  2017 

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  • ヒドロキシアセトフェノンが配位したタングステン錯体による環状オレフィンのメタセシス重合

    鳥取大会(第47回石油・石油化学討論会)  2017 

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  • シングルナノ粒子が産み出す革新素材

    イノベーション・ジャパン2017  2017 

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  • Homogeneous and Heterogeneous Ruthenium Catalysts for Hydration of Organonitriles

    BIT's 8th Annual Global Congress of Catalysis-2017  2017 

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  • シングルナノ粒子が産み出す革新素材

    イノベーション・ジャパン2017 JSTショートプレゼン  2017 

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  • シングルナノ粒子触媒が産み出す高選択的化学反応

    第21回岡山リサーチパーク研究・展示発表会  2017 

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  • 鉄酸化細菌が常温・常圧で産み出すルテニウム系触媒の可能性

    第21回岡山リサーチパーク研究・展示発表会  2017 

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  • Oxo-tungsten Complexes of Hydroxyacetophenone Derivatives as an Olefin Metathesis Precatalyst

    Symposium on Olefin Metathesis and Related Chemistry (ISOM XXII)  2017 

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  • 鉄酸化細菌を用いたAl固溶鞘状酸化鉄の作製

    第55回セラミックス基礎科学討論会  2017 

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  • 貴金属ナノ粒子を触媒とする部分水素化反応

    第119回触媒討論会  2017 

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  • Oxo-tungsten Complexes of Hydroxyacetophenone Derivatives as an Olefin Metathesis Precatalyst

    Symposium on Olefin Metathesis and Related Chemistry (ISOM XXII)  2017 

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  • 「機能性ナノ材料」科学・技術研究フォーラム

    第21回岡山リサーチパーク研究・展示発表会  2017 

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  • 2'-ヒドロキシアセトフェノンが配位したタングステン錯体の分子構造とオレフィンメタセシス機能

    第119回触媒討論会  2017 

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  • 触媒で樹脂をつくる、おもしろ体験実験 地域・産学連携による4年間の試み

    キャットケム実験室ミニシンポジウム2016  2016 

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  • Hydration of Nitriles Catalyzed by Homogeneous Iridium(I) Catalysts Having (O,O)-Chelate Ligands

    20th International Symposium on Homogeneous Catalysis (ISHC)  2016 

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  • 高濃度ギ酸から常温付近、添加物ゼロで水素を製造する化学触媒法の可能性

    第20回岡山リサーチパーク研究・展示発表会  2016 

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  • 六塩化タングステンを出発原料とする古典的なオレフィンメタセシス触媒の再検討

    第117回触媒討論会  2016 

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  • アセトフェノン誘導体を配位子にもつ オレフィンメタセシス用タングステン錯体触媒

    2016年日本化学会中国四国支部大会 香川大会  2016 

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  • 鉄酸化細菌が常温で産み出すルテニウム系ニトリル水和触媒

    第6回CSJ化学フェスタ  2016 

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  • 六塩化タングステンとカルボニル化合物から生成する錯体触媒によるオレフィンメタセシス

    第118回触媒討論会  2016 

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  • 貴金属ナノ粒子を触媒とするテルペン類の水素化反応

    第60回 香料・テルペンおよび精油化学に関する討論会  2016 

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  • Hydration of Nitriles Catalyzed by Homogeneous Iridium(I) Catalysts Having (O,O)-Chelate Ligands

    20th International Symposium on Homogeneous Catalysis (ISHC)  2016 

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  • 「機能性ナノ複合材料」科学・技術研究フォーラム

    岡山大学知恵の見本市2016  2016 

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  • 微生物が産み出す、安全で鮮やかな赤色顔料と、アミド等製造用固体触媒

    岡山大学 新技術説明会  2016 

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  • 鉄酸化細菌が常温で産み出すルテニウム系固体触媒

    岡山大学知恵の見本市2016  2016 

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  • 高濃度ギ酸から水素を製造する化学触媒法

    第13回 岡山大学-産総研 研究交流会  2015 

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  • Catalytic Hydration of Organonitriles Catalyzed by O-donor Ligated Iridium Complexes

    The 2015 International Chemical Congress of Pacific Basin Societies  2015 

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  • ROMP用工業錯体触媒におけるルテニウム中心へのNHC配位子の導入方法

    日本化学会第95春季年会  2015 

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  • Catalytic Hydration of Organonitriles Catalyzed by O-donor Ligated Iridium Complexes

    The 2015 International Chemical Congress of Pacific Basin Societies  2015 

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  • ROMP用工業錯体触媒におけるルテニウム中心へのNHC配位子の導入方法

    日本化学会第95春季年会  2015 

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  • 工業的に重要な新しいルテニウム触媒系の研究開発

    岡山地区化学工学懇話会 平成27年度特別講演会  2015 

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  • 軽量で絶縁性に優れる熱硬化性C5樹脂

    中国地域新技術・新製品展示商談会 ~ダイハツグループ向け展示商談会~  2015 

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  • 耐熱・高絶縁性C5樹脂を製造する錯体触媒のキログラム規模合成

    イノベーション・ジャパン大学見本市(JSTショートプレゼン)  2014 

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  • 軽量・高絶縁性C5樹脂を製造する工業触媒の大量製造技術の新展開

    第19回岡山リサーチパーク研究・展示発表会  2014 

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  • 軽量で絶縁性に優れる熱硬化性C5樹脂

    中国地域自動車関連技術シーズ提案会(マツダ株式会社向けシーズ提案会)  2014 

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  • ジシクロペンタジエンの開環メタセシス重合用ルテニウム触媒の工業的合成法の開発と反応射出成形法への展開

    第63回高分子討論会  2014 

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  • 反応射出成形法によるジシクロペンタジエン樹脂の製造―樹脂性能を革新する新規触媒プロセスの開発―

    旭川大会(第44回石油・石油化学討論会)  2014 

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  • 耐熱・高絶縁性C5樹脂を製造する錯体触媒のキログラム規模合成

    イノベーション・ジャパン大学見本市  2014 

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  • 軽量・高絶縁性C5樹脂を製造する工業触媒の大量製造技術の新展開

    第19回岡山リサーチパーク研究・展示発表会(プレゼンテーション)  2014 

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  • Development of Industrial Synthesis of the Ruthenium Catalyst for Ring Opening Metathesis Polymerization of Dicyclopentadiene (DCP)

    第4回触媒科学研究発表会  2013 

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  • 革新的C5樹脂

    革新的C5樹脂の産業利用  2013 

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  • 「やきもの」を用いる科学啓発活動の取り組み

    日本セラミックス協会2013年年会  2013 

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  • 錯体触媒法による次世代石油樹脂の新たな実用的製造技術の開発

    ちゅうごく産業創造センター『ビジネスマッチング交流会』  2012 

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  • Toward Industrial Applications of Homogeneous Catalysts

    HANNOVER MESSE 2012  2012 

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  • 高濃度ギ酸から水素を製造する化学触媒法

    第8回国際水素・燃料電池展 2012  2012 

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  • Homogeneous Hydration Catalysts for the Production of Acrylamide Using a Minimum Amount of Water Under Neutral Conditions

    18th International Symposium on Homogeneous Catalysis  2012 

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  • 錯体触媒法による石油樹脂の新たな実用製造技術の共同開発

    岡山大学知恵の見本市2012  2012 

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  • 低炭素社会を先導する革新的触媒技術開発

    中国地域国立5大学連携事業「化学分野における大学研究シーズ説明会」  2012 

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  • 錯体触媒法による石油樹脂の新たな実用製造技術の共同開発

    岡山大学知恵の見本市2012  2012 

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  • アクリルアミド製造用のルテニウム錯体触媒

    第110回触媒討論会  2012 

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  • アクリロニトリルの水和反応を触媒するイリジウム錯体

    秋田大会(第42回石油・石油化学討論会)  2012 

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  • 科研費以外のいわゆる競争的資金の最新動向

    平成24年度第1回研究スキルアップ講座『 知りたい!研究予算の確保と有効な使い方』  2012 

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  • Homogeneous Hydration Catalysts for the Production of Acrylamide Using a Minimum Amount of Water Under Neutral Conditions

    18th International Symposium on Homogeneous Catalysis  2012 

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  • 高濃度ギ酸から水素を製造する化学触媒法

    第8回国際水素・燃料電池展 2012 研究発表大会  2012 

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  • アクリルアミドを製造するニトリル水和用の錯体触媒

    日本化学会第92春季年会  2012 

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  • Toward Industrial Applications of Homogeneous Catalysts

    ハノーバーメッセ2012  2012 

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  • ニトリルヒドラターゼと、アクリルアミド製造用錯体触媒の作用機構の関連性

    第22回金属の関与する生体関連反応シンポジウム(SRM2012)  2012 

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  • アクリルアミドを高選択的に製造する錯体触媒法

    日本化学会第92春季年会  2012 

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  • 高選択的にアクリルアミドを製造する新たな錯体触媒の開発

    第109回触媒討論会  2012 

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  • 有機エレクトロニクス材料の中規模製造工程の開発

    中国地域太陽電池フォーラム 産学官ビジネスマッチング交流会  2011 

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  • 環境・エネルギー問題に対応する新たなナノ触媒系の開発-加水分解触媒、水素製造触媒-

    nanotech 2011 国際ナノテクノロジー総合展・技術展  2011 

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  • イリジウム錯体触媒による高濃度ギ酸からの水素製造

    第108回触媒討論会  2011 

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    INCHEM TOKYO 2011  2011 

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    ちゅうごく産業創造センター研究成果説明会  2011 

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  • 地域の産学連携による省エネ型次世代触媒技術の開発

    岡山大学知恵の見本市2011  2011 

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  • 錯体触媒を用いる高濃度ギ酸からの水素製造

    山口大会(第41回石油・石油化学討論会)  2011 

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  • 環境・エネルギー問題に対応する新たなナノ触媒系の開発-加水分解触媒、水素製造触媒-

    nanotech 2011 国際ナノテクノロジー総合展・技術展 シーズ&ニーズセミナー  2011 

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  • 色素増感型太陽電池等に適用可能な高純度金属錯体の高効率製造法

    中国地域太陽電池フォーラム産学マッチング交流会  2010 

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  • 独自開発に成功「アクリルアミド製造用の革新的化学触媒」

    イノベーションジャパン2010 大学見本市  2010 

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  • 独自開発に成功「アクリルアミド製造用の革新的化学触媒」

    イノベーションジャパン2010 大学見本市 新技術説明会  2010 

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  • 触媒的な化学合成にマイクロ波を活用するための初歩的な疑問

    四国マイクロ波プロセス研究会 第7回講演会  2010 

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  • CFRTP材料の射出成形にむけた、 熱可塑性樹脂への官能基付与・炭素繊維の表面処理等への取り組みの方向性

    先進環境対応車技術集積の形成及び事業展開プロジェクト事業 技術シーズ発信会  2010 

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  • 色素増感型太陽電池等に適用可能な高純度金属錯体の高効率製造法

    中国地域太陽電池フォーラム産学マッチング交流会  2010 

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  • アクリル系アミド類を製造する次世代化学触媒法

    岡山大学新技術説明会  2010 

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  • 単独開発に成功「アクリルアミド製造用の第4世代押木触媒」

    岡山大学知恵の見本市2010  2010 

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  • 水の資源・エネルギー問題に着目した新規ニトリル水和プロセス

    日本化学会第89春季年会  2009 

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  • 生体触媒の制約を超える人工加水分解触媒

    日本化学会第89春季年会  2009 

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  • 化学触媒法による革新的低炭素型アミド製造技術

    岡山大学新技術説明会  2009 

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  • 革新的化学触媒法による低炭素社会指向のアミド製造技術

    nanotech 2009 国際ナノテクノロジー総合展・技術展  2009 

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  • 化学触媒による極性化合物の加水分解法

    医薬品原料国際展  2009 

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  • 高純度錯体製造のための革新的低コストプロセス

    オルガテクノ2009  2009 

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  • 化学触媒がもたらす低炭素革命:知的創造サイクル循環への挑戦と課題

    第2回いちょう並木研究サロン  2009 

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  • Bio-inspired Highly Active Homogeneous Catalysts for Hydration of Nitriles: Activation of Water under Neutral Conditions

    14th International Conference on Biological Inorganic Chemistry  2009 

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  • 化学触媒による極性化合物の加水分解法

    医薬品原料国際展アカデミックフォーラムプレゼンテーション  2009 

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  • 単分散ナノ粒子の複合化による新たな触媒機能の発現

    イノベーションジャパン2009 大学見本市 新技術説明会  2009 

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  • 10 族金属ナノ粒子複合触媒を用いるニトリルの水和反応

    第104回触媒討論会  2009 

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  • 省エネ・省資源を実現する化学触媒によるニトリル水和プロセス

    第3回中四国若手CE合宿(化学工学会中国四国支部若手の会)  2009 

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  • 単分散ナノ粒子の複合化による新たな触媒機能の発現

    イノベーションジャパン2009 大学見本市  2009 

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  • 高純度錯体製造のための革新的低コストプロセス

    オルガテクノ2009  2009 

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  • 省エネ・省資源化に資する「独創的触媒機能の創出」

    岡山大学知恵の見本市2009  2009 

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  • 新規な超高活性ニトリル水和触媒の開発と応用

    地域発技術シーズ発表会〜産学官連携マッチングの場〜(JST新技術説明会)  2008 

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  • 錯体触媒法による革新的省エネルギー型アミド製造技術

    JSTつなぐしくみ新技術説明会  2008 

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  • 新規2元機能型触媒によるニトリル類の水和反応

    触媒学会50周年記念千葉地区講演会  2008 

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  • 省エネルギー型化学触媒プロセスの開発(工業化へ向けた水問題の考え方)

    香川大学「第7回遠隔教育調査研究セミナー」  2008 

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  • 廃水ゼロを実現する革新的アミド類製造プロセス

    イノベーション・ジャパン2008新技術説明会  2008 

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  • 化学触媒による廃水ゼロのアミド製造法

    オルガテクノ2008/有機テクノロジー展出展者セミナー  2008 

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  • 超低炭素社会へ向けた化学触媒の可能性

    岡山大学知恵の見本市2008  2008 

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  • 廃水ゼロを実現する革新的アミド類製造プロセス

    イノベーション・ジャパン2008  2008 

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  • 化学触媒による廃水ゼロのアミド製造法

    オルガテクノ2008/有機テクノロジー展  2008 

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  • Pyridylphosphine-Ruthenium and -Iridium Complexes: New Efficient Catalysts for the Hydration of Nitriles

    14th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 14)  2007 

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  • 中性条件でニトリルの水和反応を実現する二元機能型錯体触媒の分子設計

    触媒道場  2007 

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  • タンタル上のアルキン配位子交換反応の機構研究

    有機金属若手研究者の会  2007 

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  • THE COORDINATION MODE OF A DIPHENYL-2-PYRIDYLPHOSPHINE LIGAND TO A Ru(acac)2 AND A Ir(acac) UNITS. THE RATE ACCELERATION BY THE LIGAND IN THE CATALYTIC HYDRATION OF NITRILES

    1st Asian Conference on Coordination Chemistry  2007 

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  • イリジウム錯体触媒による新規無溶媒水和プロセス

    イノベーション・ジャパン2007大学見本市(NEDO技術シーズ発表会)  2007 

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  • 無溶媒条件下でニトリル水和反応を触媒する新規イリジウム錯体の開発

    触媒道場  2007 

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  • イリジウム錯体触媒による新規無溶媒水和プロセス

    イノベーション・ジャパン2007  2007 

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  • 最小限の水で加水分解を実現する人工触媒法の開発

    2007産学官技術交流フェア(NEDO技術シーズ発表会)  2007 

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  • シクロペンチルメチルエーテルを溶媒とする新規イリジウム錯体触媒の結晶化

    日本結晶学会年会  2007 

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  • 人工触媒による無溶媒型加水分解法の開発

    全日本科学機器展 in 大阪 2007 大学成果プレゼンテーション  2007 

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  • ニトリル類の水和を無溶媒で触媒する新規錯体触媒の開発

    札幌大会(石油学会)  2007 

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  • ニトリル類の水和反応を無溶媒で触媒する新規高活性イリジウム錯体の開発

    第100回触媒討論会(触媒討論会B)  2007 

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  • 人工触媒による無溶媒型加水分解法の開発

    全日本科学機器展 in 大阪 2007  2007 

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  • 超高活性ニトリル水和触媒の開発

    第10回岡山リサーチパーク研究・展示発表会  2006 

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  • タンタル-ピリジルホスフィン錯体の合成とその分子構造

    日本化学会第86春季年会  2006 

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  • ルテニウム錯体触媒を用いた1,4-ブタンジオールの脱水素環化反応によるγ-ブチロラクトン製造技術の開発

    日本化学会第86春季年会  2006 

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  • 新規二核有機クロム錯体の構造とオレフィンのシリルシクロプロパン化

    日本化学会第86春季年会  2006 

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  • ジフェニルアセチレンを配位子にもつタンタル-ビス(ピリジン)錯体の選択的ベンジル化

    日本化学会第86春季年会  2006 

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  • Ruthenium-Catalyzed Dehydrogenation of 1,4-Butanediol To Gamma-Butyrolactone

    Fifth Tokyo Conference on Advanced Catalytic Science and Technology  2006 

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  • ピリジルホスフィンの配位した二元機能型の新規ルテニウム、イリジウム触媒によるニトリルの水和反応

    第53回有機金属化学討論会  2006 

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  • Unusual olefin polymerization behavior of titanium catalysts containing indenyl-phenoxy ligands

    Fifth Tokyo Conference on Advanced Catalytic Science and Technology  2006 

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  • Design and Synthesis of Structurally Simple Benzensulfonanilide-type Cyclooxygenase inhibitors

    Pacifichem 2005  2005 

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  • ルテニウム錯体触媒による1,4-ブタンジオールの脱水素反応と多重結合の水和反応

    三菱化学水島事業所:ポスターセッション  2005 

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  • 新規ルテニウム錯体触媒によるニトリル水和反応 -ピリジルホスフィン配位子による加速効果-

    広島地区触媒講演会  2005 

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  • タンタル-シリルアセチレン錯体のアルキン部位の配位子交換反応

    日本化学会第85春季年会  2005 

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  • Organochromium-Mediated Heterosubstituted Cyclopropanation

    IUPAC Symposium of Organometallic Chemistry Directed toward Organic Synthesis  2005 

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  • 高活性ルテニウム錯体触媒の共同開発

    岡山リサーチパーク研究・展示発表会  2005 

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  • ジフェニル-2-ピリジルホスフィンを配位子にもつルテニウム錯体を触媒とするニトリルの水和反応

    日本化学会第84春季年会  2004 

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  • Bis(acetylacetonato)ruthenium(II) Complexes for the Catalytic Hydration of Nitriles

    14th International Symposium on Homogeneous Catalysis  2004 

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  • タンタル-ビストリメチルシリルアセチレン錯体の構造と反応性

    日本化学会第84春季年会  2004 

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  • ニトリル水和反応の触媒となる高活性ルテニウム(II) ピリジルホスフィン錯体

    第51回有機金属化学討論会  2004 

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  • η2-アルキン配位子をもつタンタル錯体とアルキン類との反応性

    第34回石油・石油化学討論会、松山大会  2004 

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  • 水晶振動子におい吸着膜に用いるシクロヘキセン環を含むアルキルジエステルの合成とそのにおい吸着能

    第20回若手化学者のための化学道場  2004 

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  • ニトリルの水和反応の触媒となる新規ルテニウムピリジルホスフィン錯体

    第50回有機金属化学討論会  2004 

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  • 遷移金属錯体の静的、動的構造をみる

    最近の岡山大学における構造科学研究  2003 

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  • ジフェニル-2-ピリジルホスフィンのRu(acac)2ユニットへの配位様式

    日本化学会春季年会  2003 

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  • η2-アルキン配位子をもつトリベンジルタンタル錯体への2,6-キシリルイソニトルの挿入反応

    日本化学会春季年会  2003 

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  • 工業化、権利化を指向した次世代錯体触媒の開発

    大学起業塾,第1回研究成果プレゼンテーション  2003 

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  • 石油化学新プロセスの誕生を目指すルテニウム錯体触媒の開発

    若手研究者・企業経営者のための知的財産活用セミナー,第4回岡山大学地域共同研究センターセミナーと共同開催  2003 

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  • アルキン配位子をもつタンタル錯体の分子構造と反応性

    第19回若手化学者のための化学道場  2003 

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  • Structures and Reactivities of Tribenzyltantalum Complexes Containing an eta2-Alkyne Ligand

    The 15th International Symposium on Olefin Metathesis and Related Chemistry (ISOM XV)  2003 

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  • ジフェニル-2-ピリジルホスフィンのRu(acac)2ユニットへの配位様式

    日本化学会第83春季年会  2003 

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  • eta2-アルキン配位子をもつトリベンジルタンタル錯体への2,6- キシリルイソニトルの挿入反応

    日本化学会第83春季年会  2003 

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  • DMFやTMEDAの配位した新規二価クロム錯体によるエチレン重合

    石油学会高山大会(第32回石油、石油化学討論会)  2002 

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  • Synthesis, Structure, and Ethylene Polymerization Behavior of Ti and Zr Complexes Bearing Imine-Phenoxy Chelate Ligands

    223rd ACS National Meeting  2002 

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  • h2-アルキン配位子をもつトリベンジルタンタル錯体の構造

    第49回有機金属化学討論会  2002 

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  • エチレン重合反応の触媒となる5配位二価クロム錯体の分子構造

    岡山大学VBL X線構造解析研究会  2002 

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  • 高分子一次ナノ構造を精密制御する次世代錯体触媒の開発

    平成13年度独創的起業化シーズ発掘事業研究成果発表会  2002 

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  • アルキンの環化三量化反応を触媒するタンタル-アルキン錯体の合成と構造

    日本化学会第80秋季年会  2001 

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  • 4配位または5配位の二価クロム錯体を用いるエチレン重合

    第48回有機金属化学討論会  2001 

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  • η2-アルキン配位子をもつトリベンジルタンタル錯体の合成と反応

    日本化学会第81春季年会  2001 

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  • ヒドロトリスピラゾリルボレートを配位子にもつTi(III), V(II)-アルデヒド錯体の合成と構造

    日本化学会第78春季年会  2000 

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  • TMEDAを配位子とする5配位2価クロム錯体の合成と構造

    日本化学会第78春季年会  2000 

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  • 極性分子の配位した二価クロム錯体を用いるアルデヒドからのアルケニルシラン合成

    日本化学会第78春季年会  2000 

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  • 脂肪族ジアミンの配位した4族金属錯体の合成と構造

    日本化学会第78春季年会  2000 

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  • 低分子分子結晶の低温データ測定

    岡山大学VBL X線構造解析研究会  2000 

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  • アルデヒドの配位した低原子価チタン、バナジウム錯体の合成と構造

    第18回有機合成化学夏季大学  2000 

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  • タンタル-アルキン錯体を触媒とする末端アルキンの環化三量化反応

    日本化学会第78春季年会  2000 

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  • タンタル-アルキン錯体へのカルボニル化合物の挿入反応

    日本化学会第78春季年会  2000 

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  • アルキニルホウ酸エステルの配位したタンタル-DME錯体の構造と反応

    日本化学会春季年会  1999 

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  • チタン(III)-TMEDA錯体によるカルボニル化合物のカップリング反応

    日本化学会春季年会  1999 

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  • ヨウ化アルキル、N-アクリロイルオキサゾリドン、アルデヒドの立体選択的な3分子連結反応

    日本化学会春季年会  1999 

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  • ランタノイドアセトニトリル錯体の合成と構造

    日本化学会春季年会  1999 

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    押木 俊之, 鎌田 満

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    Application no:JP2019041320  Date applied:2019.10.21

    Publication no:WO2020-085306  Date published:2020430

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    田村 勝徳, 久能 樹, 長岡 紀幸, 中西 真, 押木 俊之, 高田 潤

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    Applicant:国立大学法人 岡山大学

    Application no:特願2017-203223  Date applied:2017.10.20

    Announcement no:特開2018-070441  Date announced:2018.5.10

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    村中 誠, 押木 俊之

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    Applicant:国立大学法人 岡山大学

    Application no:JP2011077061  Date applied:2011.11.24

    Publication no:WO2012-070620  Date published:2012531

    Patent/Registration no:特許第5920834号  Date registered:2016.4.22 

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  • 金属錯体化合物及び当該金属錯体化合物を利用したアミド類の製造方法

    押木 俊之, 村中 誠

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    Applicant:国立大学法人 岡山大学

    Application no:JP2011067531  Date applied:2011.7.29

    Publication no:WO2012-017966  Date published:201229

    Patent/Registration no:特許第5732678号  Date registered:2015.4.24 

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    Applicant:DOWAホールディングス株式会社

    Application no:特願2009-179423  Date applied:2009.7.31

    Announcement no:特開2011-032205  Date announced:2011.2.17

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    Work type:Artistic work  

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  • フラミンゴの赤ちゃん

    2007

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    Work type:Artistic work  

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  • 線香花火

    2007

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    Work type:Artistic work  

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Awards

  • 第8回村川技術奨励賞

    2013.5   山陽技術振興会   新用途向けグレードの石油樹脂を提供する新たな触媒技術の開発

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    Country:Japan

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  • 岡山工学振興会科学技術賞

    2012  

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    Country:Japan

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  • ATP(アドバンスト・テクノロジー・プログラム)注目ポスター

    2012  

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    Country:Japan

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  • 日本化学会第11回技術進歩賞

    2006   日本化学会   ルテニウム錯体触媒を用いた1,4-ブタンジオールの脱水素環化反応によるγ-ブチロラクトンの製造技術の開発

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    Country:Japan

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  • 岡山リサーチパーク研究展示発表会奨励賞

    2006  

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    Country:Japan

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  • 日本化学会BCSJ賞

    2001  

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    Country:Japan

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  • 日本化学会第74春季年会ポスター賞

    1998  

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    Country:Japan

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  • 日本化学会第72春季年会ポスター賞

    1997  

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    Country:Japan

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Research Projects

  • Development of a New Synthesis Method Mimicking Iron-oxidizing Bacteria for Highly Chromatic Inorganic Pigments

    Grant number:20K21238  2020.07 - 2022.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Challenging Research (Exploratory)

    NAKANISHI Makoto

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    Grant amount:\6370000 ( Direct expense: \4900000 、 Indirect expense:\1470000 )

    Red pigments utilizing iron hydroxide produced by iron-oxidizing bacteria in nature are known to be vivid and highly heat-resistant. Based on this reaction mechanism, we attempted to develop a new synthetic process for the efficient mass production of highly saturated inorganic pigments using organic molecules. By examining the synthesis conditions in detail, we obtained inorganic pigments that exhibit color tones comparable to those of commercial pigments through a new synthesis process that is easy to scale up and suitable for mass production.

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  • New heterogeneous acid catalyst using a mesoporus organosilica as a support

    Grant number:24560947  2012.04 - 2015.03

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)  Grant-in-Aid for Scientific Research (C)

    OSHIKI Toshiyuki

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    Grant amount:\5460000 ( Direct expense: \4200000 、 Indirect expense:\1260000 )

    Several new ruthenium and iridium complexes for supported catalyst were synthesized, These complexes act as a catalyst for hydration of nitriles under neutral conditions.

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  • アクリルアミド製造用の錯体触媒を長寿命化する、新たな固定化方法の開発

    2011 - 2012

    産学が連携した研究開発成果の展開 研究成果展開事業 研究成果最適展開支援プログラム(A-STEP) 探索タイプ 

    押木 俊之

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    アクリロニトリル水溶液から50%アクリルアミド水溶液を直接製造できる、ラボレベルの固定化触媒を開発することを目標とした。アクリルアミドを高選択的に製造できるルテニウム錯体触媒をベースとする、新たな固定化方法の開発を進めた。固定化のための錯体触媒の化学修飾条件の探索および固定化条件の最適化を進め、固定化における技術的な課題を明確にした。研究開発と並行し、コーディネーターと連携しながら産業界の意見聴取を進め、本研究開発の方向性が妥当性であることを確認した。本研究開発で明らかになったグラムスケール(ラボレベル)での固定化触媒製造条件の確立を踏まえ、今後は研究成果物の知財確保を本学知的財産本部等と連携し進める予定である。

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  • バイオ水素を製造する「創エネ型」化学触媒プロセスの開発

    2009

    産学が連携した研究開発成果の展開 研究成果展開事業 地域事業 地域イノベーション創出総合支援事業 シーズ発掘試験 

    押木 俊之

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    低炭素社会づくりに資する非枯渇資源からのクリーンエネルギー確保は、我が国に課せられた緊急課題である。本課題では、代表研究者が進めてきた加水分解触媒の開発中に、偶然に発見した新規脱水素触媒をバイオ水素製造へ適用し、「創エネ型」化学触媒プロセスの基礎を構築する。

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  • バイオディーゼルを高速1段製造する実用的触媒法の開発

    2008

    産学が連携した研究開発成果の展開 研究成果展開事業 地域事業 地域イノベーション創出総合支援事業 シーズ発掘試験 

    押木 俊之

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    低炭素社会を見据えたクリーンエネルギー確保は、我が国に課せられた緊急課題である。本課題では、代表研究者が独自に発見した新規触媒系をバイオディーゼル(FAME)1段階製造法へ適用検討する。そして、現行法では原理的に実現できない実用的な高速製造法実現への目処をつける。

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  • 新規な超高活性ニトリル水和触媒の開発と応用

    2005

    産学が連携した研究開発成果の展開 研究成果展開事業 地域事業 地域イノベーション創出総合支援事業 シーズ発掘試験 

    押木 俊之

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    ニトリル類の水和反応を触媒する錯体触媒について下記の2点の研究開発を行う。目的とする反応は3-シアノピリジンの水和によるニコチンアミドの合成反応であり、工業的に価値ある反応である。この触媒は代表研究者が独自に開発した新規ルテニウム錯体(左図)であり、人工触媒としては世界最高レベルの触媒性能を誇り、ニトリルからアミドを定量的に得ることができる。(1)工業化に必要なさらなる高活性化を触媒の改良により実現(2)ニトリル以外の不飽和有機化合物の水和反応への応用

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  • Development of Highly Efficient Synthetic Reactions by Controlling Electron-Transfer Processes with a Combination of Different Metals

    Grant number:16350057  2004 - 2006

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    TAKAI Kazuhiko, OSHIKI Toshiyuki, KUNINOBU Yoichiro

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    Grant amount:\15900000 ( Direct expense: \15900000 )

    The following stereoselective reactions are developed by controlling electron-transfer processes. (1) Cross-Coupling Reactions of Alkynes and Aldehydes Leading to Allylic Alcohols by a Combination of Chromium(II), a Catalytic Amount of Nickel(II), and Water. (2) Preparation of Cyclopropylsilanes from Terminal Alkenes with Organochromium Reagents. (3) Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt and Zinc (or Manganese). (4) Mechanistic Study of Ligand Exchange Reactions of η^-TaCl_3(Me_3SiC=CSiMe_3)(dme) with Internal Alkynes. (5) Cyclotrimerization of Terminal Alkynes with a Catalytic Amount of η^2-TaCl_3(Me_3SiC=CSiMe_3)(dme).
    In addition, we developed novel organic reactions based on carbon-hydrogen bond activation with rhenium catalysts : (6) Rhenium-Catalyzed Formation of Indene Frameworks via C-H Bond Activation from Aromatic Aldimines and Acetylenes ; (7) Insertion of Polar Unsaturated Molecules into Carbon-Rhenium Bonds Generated by C-H Bond Activation: Synthesis of Isobenzofuran and Phthalimidine Derivatives ; (8) Rhenium-and Aniline-Catalyzed One-Pot Annulation of Aromatic Ketones and α,β-Unsaturated Esters Initiated by C-H Bond Activation.

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  • Development of Novel Stereoselective Pinacol Coupling Reactions

    Grant number:12450365  2000 - 2002

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

    TAKAI Kazuhiko, OSHIKI Toshiyuki

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    Grant amount:\15000000 ( Direct expense: \15000000 )

    The following stereoselective pinacol-type reactions are developed. (1) A cross-pinacol-type coupling reaction of α,β-unsaturated ketones and aldehydes is accomplished with CrCl_2 and Me_3SiCl in DMF. The diastereoselectivity of the reaction is proved to depend on the reaction temperature. (2) A cross-coupling reaction of oxygen-substituted dienes and aldehydes leading to 1,2-diol derivatives is performed with CrCl_2 in the presence of a catalytic amount of B_<12> and water. (3) A dl-selective pinacol-coupling reaction of aliphatic aldehydes is achieved with CrCl_2, manganese, and Me_3SiCl.
    In addition, we collected information on the pinacol coupling reactions with low-valent metals. (1) A titanium(III) complex TiCl_3(tmeda)(thf) which is effective for a dl-selective pinacol-coupling of aromatic aldehydes, is isolated, and the molecular structure of the complex are examined by X-ray crystallographic analysis. (2) Titanium(III) and vanadium(III) complexes having a Tp ligand are isolated, and the structure of an aldehyde-coordinated vanadium(III) complex is determined by X-ray crystallographic analysis.

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  • 水分子の配位した遷移金属錯体の構造と反応性

    Grant number:11740401  1999 - 2000

    日本学術振興会  科学研究費助成事業 奨励研究(A)  奨励研究(A)

    押木 俊之

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    Grant amount:\2200000 ( Direct expense: \2200000 )

    本年度は,水分子の配位した遷移金属錯体(アコ錯体)の反応性を検討した.前年度に合成と構造解析を行った,無水の二価のサマリウム,ユーロピウム,クロム錯体と水分子の反応性,さらに生成するアコ錯体の反応を調べた.
    二価サマリウム錯体と水分子の反応を検討した.サマリウム錯体に加える水の量により,生成する錯体構造が変化することを紫外-可視吸収スペクトルにより解明した.加えた水分子はサマリウムに配位し,アコ錯体が生成するが,溶液中で解離したまま存在する水分子も存在することがわかった.すなわち,水分子は金属へ強固に配位するのではなく,有機溶媒中では解離することも明らかになった.
    さらに,二価クロム錯体,CrCl2(dmf)(DMF=ジメチルホルムアミド),CrCl2(tmeda)(dmf)(TMEDA=テトラメチルエチレンジアミン)と水との反応では,クロム錯体が低配位の配位不飽和化学種であるにもかかわらず,クロムへの配位が起こらないことがわかった.すなわち,水分子は中心金属の違いにより,強固に配位する場合と,ほとんど配位せず配位圏外に存在する場合があることがわかった.
    このように,いくつかの金属錯体と水分子との反応を検討し,金属元素の違いにより有機溶媒中で水が異なる挙動を示すことを明らかにした.

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  • 水分子の配位した希土類錯体の構造と反応性の研究

    Grant number:98J06079  1998

    日本学術振興会  科学研究費助成事業 特別研究員奨励費  特別研究員奨励費

    押木 俊之

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    Grant amount:\1500000 ( Direct expense: \1500000 )

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  • Experiment for Chemistry and Biotechnology 1 (2023academic year) 1st and 2nd semester  - 月5~8

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Social Activities

  • 樹脂はどのようにできるか?

    Role(s):Lecturer

    大学コンソーシアム岡山  吉備創生カレッジ  2021.10.4

  • 工学安全概論

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    岡山県教育委員会  令和3年度免許法認定講習  2021.8.24