The ortho-substituent on 2,4-bis(trifluoromethyl) phenylboronic acid catalyzed dehydrative condensation between carboxylic acids and amines

2,4-Bis(trifluoromethyl) phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation. This catalyst works for a-dipeptide synthesis.