Vanadium-catalyzed solvent-free synthesis of quaternary α-trifluoromethyl nitriles by electrophilic trifluoromethylation

Abstract

The direct electrophilic trifluoromethylation of silyl ketene imines (SKIs) with hypervalent iodine reagents leads to the formation of quaternary α-trifluoromethyl nitriles in good yields. This new reaction has been carried out with a variety of substituted SKIs under solvent-free conditions using a vanadium(IV) catalyst (5 mol%). The corresponding products may be transformed into useful organofluorine building blocks. Not only copper! Oxovanadium(IV) complexes catalyze the trifluoromethylation of silyl ketene imines with hypervalent iodine reagents to form quaternary α-trifluoromethyl nitriles under solvent-free conditions. The products, formed in up to 93% yield, may be further transformed into useful synthetic building blocks for organofluorine chemistry.