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N-heterocyclic carbene catalyzed trifluoromethylation of carbonyl compounds. 2005
Jinhua J Song, and
Zhulin Tan, and
Jonathan T Reeves, and
Fabrice Gallou, and
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, USA. jsong@rdg.boehringer-ingelheim.com
[reaction: see text]. A novel N-heterocyclic carbene (NHC) catalyzed trifluoromethylation reaction of carbonyl compounds was discovered. Both enolizable and nonenolizable aldehydes and alpha-keto esters undergo facile trifluoromethylation with TMSCF3 at room temperature in the presence of only 0.5-1 mol % of the commercially available NHC (1), providing CF3-substituted alcohols in good yields. Selective trifluoromethylation of aldehydes over ketones can be achieved under NHC catalysis. These conditions are mild and simple and tolerate a variety of functional groups.
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