Activation of TMSCN by N-heterocyclic carbenes for facile cyanosilylation of carbonyl compounds.
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.
Song
Jinhua J
JJ
Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368, USA. jsong@rdg.boehringer-ingelheim.com
Gallou
Fabrice
F
Reeves
Jonathan T
JT
Tan
Zhulin
Z
Yee
Nathan K
NK
Senanayake
Chris H
CH
D000098:Acetophenones / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000098:Acetophenones; D001547:Benzaldehydes; D003486:Cyanides; D006838:Hydrocarbons; D009570:Nitriles; D014297:Trimethylsilyl Compounds; C100076:mesoxalonitrile; C030011:carbene; C058010:trimethylsilyl cyanide; D008697:Methane; C038699:acetophenone; C032175:benzaldehyde