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

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

doi:10.1016/j.tetlet.2009.05.112

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

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

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

55 Citations (Scopus)

Abstract

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

Original language	English
Pages (from-to)	4643-4646
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2009.05.112
Publication status	Published - Aug 12 2009

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.05.112

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

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

author = "Yasushi Nishihara and Eiji Inoue and Daisuke Ogawa and Yoshiaki Okada and Shintaro Noyori and Kentaro Takagi",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas {\textquoteleft}Advanced Molecular Transformations of Carbon Resources{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Y.N. is grateful to Chisso Petrochemical Corporation for generous donation of trimethylsilylacetylene to prepare 1 . ",

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T1 - Palladium/copper-catalyzed sila-Sonogashira reactions of aryl iodides with alkynylsilanes via a direct C-Si bond activation

AU - Nishihara, Yasushi

AU - Inoue, Eiji

AU - Ogawa, Daisuke

AU - Okada, Yoshiaki

AU - Noyori, Shintaro

AU - Takagi, Kentaro

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas ‘Advanced Molecular Transformations of Carbon Resources’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Y.N. is grateful to Chisso Petrochemical Corporation for generous donation of trimethylsilylacetylene to prepare 1 .

PY - 2009/8/12

Y1 - 2009/8/12

N2 - The palladium-catalyzed cross-coupling reactions of aryl iodides with alkynylsilanes in the presence of a substoichiometric amount (50 mol %) of copper(I) chloride as an activator in DMF under strictly non-basic reaction conditions afford the corresponding unsymmetrical diarylethynes in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible.

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

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

Abstract

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