Regioselective heterofunctionalization of alpha-aryl amides with heteroatom nucleophiles via electrophilic activation

Abstract

A general and efficient strategy for the α-heterofunctionalization of aryloxy-activated amides with various nucleophiles, including amines, alcohols, phenols, carboxylic acids, and thiols, has been developed. This reaction proceeded under mild reaction conditions with excellent regioselectivity, and TEA was used as the sole additive. The synthetic value of this method was demonstrated by the late-stage modification of biological molecules. Furthermore, a preliminary mechanism for this umpolung reaction has been proposed.