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

Chemoselective alpha-acylation of tertiary amides proceeded with highly electrophilic acid anhydrides and weak bases under mild conditions. beta-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 alpha-acylation.