☆ 4.8 Article

Rhodium-Catalyzed Coupling of 2-Silylphenylboronic Acids with Alkynes Leading to Benzosiloles: Catalytic Cleavage of the Carbon-Silicon Bond in Trialkylsilyl Groups

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Volume 131, Issue 22, Pages 7506-+

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ja9022978

Keywords

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Categories

Chemistry, Multidisciplinary

Funding

Synergy of Elements [19027037]
Program of Promotion of Environmental Improvement to Enhance Young Researchers' Independence
Special Coordination Funds for Promoting Science and Technology, Ministry of Education, Culture, Sports, Science and Technology (NEXT), Japan

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Abstract

The reaction of 2-(trimethylsilyl)phenylboronic acid with alkynes in the presence of a rhodium catalyst affords benzosilole derivatives. The arylvinylrhodium intermediate undergoes formal substitution at a silicon center, resulting in the cleavage of a robust silicon-methyl bond in the trimethylsilyl group.

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