N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: Electrophilic fluorination of imines and some methyl-substituted pyridines

Article abstract of DOI:10.1016/0040-4020(95)00884-B

Direct fluorination of imines with N-fluoro-bis[(trifluoromethyl)sulfonyl]imide 1 afforded mono and/or difluoroketones without the need of a strong base to first generate the imine anions. Structurally related 2- and 4-methyl-substituted pyridines gave the respective fluoromethyl pyridines with 1. Our results suggest that an enamine intermediate plays a key role in these reactions.