Copper-catalyzed synthesis of primary amides through reductive N–O cleavage of dioxazolones

Abstract

A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction conditions allow the transformation of dioxazolones to primary amides, in which sensitive functional groups such as hydroxyl, aldehyde, trialkylsilyl, and unsaturated carbon units are tolerated with excellent chemoselectivity.