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Activation of TMSCN by N-Heterocyclic Carbenes for Facile Cyanosilylation of Carbonyl Compounds

Jinhua J. Song,* Fabrice Gallou, Jonathan T. Reeves, Zhulin Tan, Nathan K. Yee and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email: jsongrdg.boehringer-ingelheim.com

J. J. Song, F. Gallou, J. T. Reeves, Z. Tan, N. K. Yee, C. H. Senanayake, J. Org. Chem., 2006, 71, 1273-1276.

DOI: 10.1021/jo052206u


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Abstract

N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile and mild cyanosilylation of carbonyl compounds. Various trimethylsilylated cyanohydrins were isolated in very good to excellent yields.

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proposed mechanism



Key Words

Cyanosilylation, Organocatalysis


ID: J42-Y2006-340