Preparation of α-silyl- or α,α-bis(silyl)-substituted alkylcopper reagents and their synthetic use

Junichi Kondo, Atsushi Inoue, Yuki Ito, Hiroshi Shinokubo and Koichiro Oshima

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto Daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email: oshimaorgrxn.mbox.media.kyoto-u.ac.jp

J. Kondo, A. Inoue, Y. Ito, H. Shinokubo, K. Oshima, Tetrahedron, 2005, 61, 3361-3369.

DOI: 10.1016/j.tet.2005.01.101

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Abstract

Treatment of chlorobis(methyldiphenylsilyl)methyllithium with various Grignard reagents and CuCN·2LiCl afforded 1,1-disilylalkylcopper species. Subsequent aerobic oxidation provided various acylsilanes in good yields. The preparation of 1-cyano-1-silylalkylcopper species via consecutive double 1,2-migration of alkyl and cyano groups is described.

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Key Words

Acylsilanes, Carbenoids, 1,2-Migration, Organocopper reagents, Halogen-lithium exchange, Grignard reagents, Air

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ID: J72-Y2005-2880