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

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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 jsong@rdg.boehringer-ingelheim.com

J. Org. Chem., 2006, 71 (3), pp 1273–1276

DOI: 10.1021/jo052206u

Publication Date (Web): January 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

N-Heterocyclic carbenes were found to be highly effective organocatalysts in activating TMSCN for facile cyanosilylation of carbonyl compounds. Cyano transfer from TMSCN to aldehydes and ketones proceeds at room temperature in the presence of only 0.01−0.5 mol % of N-heterocyclic carbene (1), leading to a range of trimethylsilylated cyanohydrins in very good to excellent yields. These conditions are extremely mild and simple and tolerate various functional groups.

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Published In Issue February 03, 2006
Received October 23, 2005

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