Chemoselective α-Trifluoroacetylation of Amides Using Highly Electrophilic Trifluoroacetic Anhydrides and 2,4,6-Collidine.

Abstract

Chemoselective α-acylation of tertiary amides proceeded with highly electrophilic acid anhydrides and weak bases under mild conditions. β-Ketoamides containing trifluoroacetyl or perfluoroacyl groups were selectively obtained even in the presence of other functional groups such as ketone, ester, etc. Density functional theory calculations suggest that 1-acyloxyenamine is the key intermediate for the chemoselective α-acylation.