HBF4-mediated direct alcoholysis of amides under mild conditions

Abstract

A metal-free, HBF₄-mediated alcoholysis of amides under relatively mild conditions is reported. This operationally simple process provides a new route to amide–ester bond conversion with excellent chemoselectivity. In particular, a wide range of primary, secondary and tertiary amides, including the challenging thioamides, can be esterified in very high yields. In addition, this transformation does not require the use of additional solvent, and many products can be obtained by washing with water.