Faculty Profiles - NISHIHARA Yasushi

Papers - NISHIHARA Yasushi

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Recent Advances in Transition-metal-catalyzed C-C Bond Formation via C(sp2)-F Bond Cleavage Reviewed

Liyan Fu, Qiang Chen, Yasushi Nishihara

Chemical Records 21 ( 12 ) 3394 - 3410 2021.4

Palladium-catalyzed decarbonylative and decarboxylative cross-coupling of acyl chlorides with potassium perfluorobenzoates affording unsymmetrical biaryls Reviewed

Liyan Fu, Jingwen You, Yasushi Nishihara

Chemical Communications 57 ( 30 ) 3696 - 3699 2021.3

Synthesis and reactivity of boryloxorhodium complexes. Relevance to intermolecular transmetalation from boron to Rhodium in Rh-catalyzed reactions Reviewed

Yasushi Nishihara, Yasuhiro Nishide, Kohtaro Osakada

Dalton Transactions 50 ( 10 ) 3610 - 3615 2021.2

Authorship：Lead author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：Royal Society of Chemistry (RSC)

<p>The synthesis of a dimeric boryloxorhodium complex having the Rh–O–Bpin scaffold from the reaction of [(cod)Rh(OMe)]2 or [(cod)Rh(OH)]2 with an arylboronate has been achieved. The obtained dirhodium complex is converted...</p>

DOI： 10.1039/d1dt00440a

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Synthesis of 2-Isoxazoline N-Oxides by Copper-Mediated Radical Annulation of Alkenes with α-Nitrobenzyl Bromides Reviewed

Masayuki Iwasaki, Yuichi Ikemoto, Yasushi Nishihara

Organic Letters 22 ( 19 ) 7577 - 7580 2020.10

Synthesis of Oxygen-Containing Heterocyclic Compounds by Iron-Catalyzed Alkylative Cyclization of Unsaturated Carboxylic Acids and Alcohols Reviewed

Masayuki Iwasaki, Yasuki Kazao, Takumi Ishida, Yasushi Nishihara

Organic Letters 22 ( 18 ) 7343 - 7347 2020.9

Efficient Synthesis of π-Conjugated Organic Molecules Utilizing Cross─Coupling Reactions and Application to Electronic Devices Invited Reviewed

Yasushi Nishihara

J. Syn. Org. Chem. Jpn. 78 ( 9 ) 867 - 874 2020.9

Authorship：Lead author,　Corresponding author Language：Japanese Publisher：The Society of Synthetic Organic Chemistry, Japan

The development of efficient synthetic methods of π-conjugated compounds by means of cross-coupling reactions are reported. Tetraarylethenes with four different substituents are synthetic targets. The Pt-catalyzed addition of diboron to alkynylsilanes to yield 1-aryl-1-silyl-2,2-diborylethenes with perfect stereoselectivity. Step by step chemoselective Suzuki-Miyaura couplings with aryl halides were performed to give a triarylsilylethene with perfect chemoselectivity. The silyl group was transformed to the aryl group with desilybromination, followed by Suzuki-Miyaura coupling, leading to the successful synthesis of the desired tetraarylated olefin. On the other hand, novel and versatile methods for the synthesis of various phenacene and thienophenacene derivatives by cross-coupling reactions were elucidated for application to organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). As one of representative phenacenes, picene is a polycyclic aromatic hydrocarbon consisting of five fused benzene rings with a W-shape structure, which exhibits high hole mobility. We successfully found the synthetic route of various substituted picenes. In addition, the synthesis of phenanthro [1,2-b : 8,7-b’] dithiophene (PDT) was achieved by replacing two terminal phenyl rings in picene with thiophene rings. The fabricated OFET devices based on C₁₂-PDT-2 displayed a quite high mobility of up to 5.6 cm² V⁻¹ s⁻¹. In regard to OPV devices, PDT-fluorinated benzothiadiazole (BT) polymers possessing alkyl side chains showed the highest power conversion efficiencies (PCE) of 9.0%.

DOI： 10.5059/yukigoseikyokaishi.78.867

CiNii Article

CiNii Books

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Other Link： https://ndlsearch.ndl.go.jp/books/R000000004-I030651888

Synthesis and Physicochemical Properties of 2,7-Disubstituted Phenanthro[2,1-b:7,8-b’]dithiophenes Reviewed

Zhenfei Ji, Zeliang Cheng, Hiroki Mori, Yasushi Nishihara

Molecules 25 ( 17 ) 3842 - 3842 2020.8

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：MDPI AG

We report the design, synthesis, and physicochemical properties of an array of phenanthro[2,1-b:7,8-b’]dithiophene (PDT-2) derivatives by introducing five types of alkyl (CnH2n+1; n = 8, 10, 12, 13, and 14) or two types of decylthienyl groups at 2,7-positions of the PDT-2 core. Systematic investigation revealed that the alkyl length and the type of side chains have a great effect on the physicochemical properties. For alkylated PDT-2, the solubility was gradually decreased as the chain length was increased. For instance, C8-PDT-2 exhibited the highest solubility (5.0 g/L) in chloroform. Additionally, substitution with 5-decylthienyl groups showed poor solubility in both chloroform and toluene, whereas PDT-2 with 4-decylthienyl groups resulted in higher solubility. Furthermore, UV-vis absorption of PDT-2 derivatives substituted by decylthienyl groups showed a redshift, indicating the extension of their π-conjugation length. This work reveals that modification of the conjugated core by alkyl or decylthienyl side chains may be an efficient strategy by which to change the physicochemical properties, which might lead to the development of high-performance organic semiconductors.

DOI： 10.3390/molecules25173842

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Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates Reviewed

Liyan Fu, Qiang Chen, Yasushi Nishihara

Organic Letters 22 ( 16 ) 6388 - 6393 2020.8

Syntheses of polynorbornadienes by ring-opening metathesis polymerizations of symmetric and non-symmetric 2,3-bis(alkoxycarbonyl)norbornadienes and their conversion to half-ester derivatives Reviewed

Jianjun Shi, Yuki Hayashishita, Toshikazu Takata, Yasushi Nishihara, Satomi Niwayama

Organic & Biomolecular Chemistry 18 ( 34 ) 6634 - 6642 2020.7

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes Reviewed

Qiang Chen, Liyan Fu, Yasushi Nishihara

Chemical Communications 56 ( 57 ) 7977 - 7980 2020.6

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions Reviewed

Xiu Wang, Zhenhua Wang, Takumi Ishida, Yasushi Nishihara

Journal of Organic Chemistry 85 ( 11 ) 7526 - 7533 2020.4

Synthesis of Dinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (DNADT) Derivatives: Effect of Alkyl Chains on Transistor Properties Invited Reviewed

Takumi Ishida, Yuta Sawanaka, Ryota Toyama, Zhenfei Ji, Hiroki Mori, Yasushi Nishihara

International Journal of Molecular Sciences 21 ( 7 ) 2447 - 2447 2020.4

Authorship：Last author,　Corresponding author Language：English Publishing type：Research paper (scientific journal) Publisher：MDPI AG

To investigate organic field-effect transistor (OFET) properties, a new thienoacene-type molecule, 4,14-dihexyldinaphtho[2,3-d:2’,3’-d’]anthra[1,2-b:5,6-b’]dithiophene (C6-DNADT), consisting of π-conjugated nine aromatic rings and two hexyl chains along the longitudinal molecular axis has been successfully synthesized by sequential reactions, including Negishi coupling, epoxidation, and cycloaromatization. The fabricated OFET using thin films of C6-DNADT exhibited p-channel FET properties with field-effect mobilities (µ) of up to 2.6 × 10−2 cm2 V−1 s−1, which is ca. three times lower than that of the parent DNADT molecule (8.5 × 10−2 cm2 V−1 s−1). Although this result implies that the installation of relatively short alkyl chains into the DNADT core is not suitable for transistor application, the origins for the FET performance obtained in this work is fully discussed, based on theoretical calculations and solid-state structure of C6-DNADT by grazing incidence wide-angle X-ray scattering (GIWAXS) and atomic force microscopy (AFM) analyses. The results obtained in this study disclose the effect of alkyl chains introduced onto the molecule on transistor characteristics.

DOI： 10.3390/ijms21072447

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Palladium-Catalyzed Decarbonylative Alkylation of Acyl Fluorides Reviewed

Liyan Fu, Qiang Chen, Zhenhua Wang, Yasushi Nishihara

Organic Letters 22 ( 6 ) 2350 - 2353 2020.3

Nickel or Palladium-Catalyzed Decarbonylative Transformations of Carboxylic Acid Derivatives Reviewed

Zhenhua Wang, Xiu Wang, Yasushi Nishihara

Chemistry An Asian Journal 15 ( 8 ) 1234 - 1247 2020.3

Copper-Catalyzed Regioselective Aminothiolation of Aromatic and Aliphatic Alkenes with N-Fluorobenzenesulfonimide and Thiols through Three-Component Radical Coupling Reviewed

Masayuki Iwasaki, Kosei Nonaka, Song Zou, Yuta Sawanaka, Takaaki Shinozaki, Tomoya Fujii, Kiyohiko Nakajima, Yasushi Nishihara

The Journal of Organic Chemistry 84 ( 23 ) 15373 - 15379 2019.12

Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides Reviewed

Zhenhua Wang, Xiu Wang, Yasuyuki Ura, Yasushi Nishihara

Organic Letters 21 ( 17 ) 6779 - 6784 2019.9

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

Yuya Asanuma, Hiroki Mori, Yasushi Nishihara

Chemistry Letters 48 ( 9 ) 1029 - 1031 2019.9

Nickel/copper-cocatalyzed decarbonylative silylation of acyl fluorides Reviewed

Wang Xiu, Wang Zhenhua, Nishihara Yasushi

Chemical Communications 55 ( 71 ) 10507 - 10510 2019.8

PPh3-Assisted Esterification of Acyl Fluorides with Ethers via C(sp3)–O Bond Cleavage Accelerated by TBAT Invited Reviewed

Zhenhua Wang, Xiu Wang, Yasushi Nishihara

Catalysts 9 ( 7 ) 574 - 574 2019.6

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

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

Bulletin of the Chemical Society of Japan 92 ( 6 ) 1107 - 1116 2019.5

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Papers - NISHIHARA Yasushi