title: N-heterocyclic carbene catalyzed trifluoromethylation of carbonyl compounds.
abstract: [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.
authors.affiliation: 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
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Fabrice
authors.initials: F
authors.lastname: Gallou
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake