Rhodium-Catalyzed Carbon-Cyano Bond Cleavage Reactions Using Organosilicon Reagents

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概要

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• Rhodium-catalyzed carbon-cyano bond cleavage reactions using organosilicon reagents are described. When disilane is used as the silicon reagent, the C-CN bonds in aryl and alkenyl cyanides are silylated to form the corresponding silylated products along with silyl cyanide. Reductive decyanation of nitriles is achieved when hydrosilane is used as the silicon reagent. In addition, this catalytic system can be applied to the C(sp3)-CN bonds in simple aliphatic nitriles. In both reactions, the silylrhodium species generated in situ serves as a catalytically active species, cleaving C-CN bonds via an η2-iminoacyl complex. Addition of external electrophiles allowed the silicon-assisted cleavage of C-CN bonds to be applied to C-C bond formation reactions. Intramolecular arylation of benzonitrile bearing a tethered chlorophenyl group and decyanative Mizoroki-Heck-type alkenylation of nitriles with vinylsilanes have been developed.

• 社団法人 有機合成化学協会の論文
• 2010-11-01

著者

• Kita Yusuke

  Faculty Of Engineering Osaka University

• Chatani Naoto

  Frontier Research Base For Global Young Researchers Graduate School Of Engineering Osaka University

• TOBISU Mamoru

  Faculty of Engineering, Osaka University

• Tobisu Mamoru

  Faculty Of Engineering Osaka University

関連論文

• Rhodium-Catalyzed Carbon-Cyano Bond Cleavage Reactions Using Organosilicon Reagents

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