Nucleophilic Trifluoromethylation of Imines under Acidic Conditions

Abstract

Abstract A general method for the trifluoromethylation of imines by using Me 3 SiCF 3 under acidic conditions is described. The reaction is promoted by hydrofluoric acid generated in situ from KHF 2 and either TFA or TfOH. A new chemoselectivity pattern was achieved, as the C=N bond was found to be more reactivate than the carbonyl group. The trifluoromethylation reaction is believed to proceed by concerted transfer of the CF 3 group from the silicon atom to the iminium electrophile. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)