Generation of Iminyl Copper Species from α-Azido Carbonyl Compounds and Their Catalytic C−C Bond Cleavage under an Oxygen Atmosphere

Abstract

A copper-catalyzed reaction of alpha-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from alpha-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O(2) was found to be incorporated into the beta-carbon fragment as a carboxylic acid.