研究者詳細 - 西原　康師

論文 - 西原　康師

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

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

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

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

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

DOI： 10.1021/jo000679p

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

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

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

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

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

DOI： 10.1246/bcsj.73.1409

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

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

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

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

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

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

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

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

DOI： 10.1246/bcsj.73.985

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

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

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

記述言語：英語出版者・発行元：AMER CHEMICAL SOC

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

DOI： 10.1021/jo991686k

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

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

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

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

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

DOI： 10.1246/bcsj.73.749

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

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

POLYHEDRON 19 ( 5 ) 567 - 568 2000年3月

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

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

DOI： 10.1016/S0277-5387(99)00409-X

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

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

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

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

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

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

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

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

DOI： 10.1021/om990103u

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Palladium-catalyzed carbon-carbon bond-forming reactions of silanols. 査読

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

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 218 U101 - U101 1999年8月

Homo- and cross-coupling reactions of alkynylsilanes mediated by a copper(I) salt. 査読

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

ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 218 U195 - U195 1999年8月

Synthesis and optical resolution of novel chiral silanols

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

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

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

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

DOI： 10.1246/cl.1999.549

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

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

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

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

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

DOI： 10.1021/ol990614c

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

H Kajiro, A Mori, Y Nishihara, T Hiyama

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

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

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

DOI： 10.1246/cl.1999.459

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

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

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

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

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

DOI： 10.1016/S0040-4020(99)00141-6

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

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

SYNLETT ( 1 ) 99 - 101 1999年1月

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

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

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A facile preparation and cyclopropanation of 1-alkenylsilanols 査読

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

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

記述言語：英語出版者・発行元：The Chemical Society of Japan

Alkenylsilanols are prepared by the reaction of hexamethyltrisiloxane (D₃) with alkenyllithiums or alternatively by the reaction of cyclic siloxanes substituted by an alkenyl group with organolithiums and transformed to the corresponding cyclopropylsilanols using diiodomethane and diethylzinc. Lithium alkenylsilanolates, primary products of the preparation, also undergo cyclopropanation. As in the case of allylic alcohols, the silanol functionality is found to enhance the rate of cyclopropanation compared with that of alkenyltrialkylsilane or alkoxydialkylsilane. The obtained cyclopropylsilanols are further converted into the corresponding cyclopropanols by the Tamao oxidation.

DOI： 10.1246/bcsj.71.2409

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その他リンク： http://orcid.org/0000-0002-1163-264X

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

Nishihara Y, Ikegashira K, Mori A, Hiyama T

Tetrahedron Letters 39 ( 23 ) 4075 - 4078 1998年

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

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

Chemistry Letters 1998 ( 5 ) 443 - 444 1998年

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

Hirabayashi K, Nishihara Y, Mori A, Hiyama T

Tetrahedron Letters 39 ( 43 ) 7893 - 7896 1998年

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