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

A copper-catalyzed reaction of a-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.