Coupling of Methyl Ketones and Primary or Secondary Amines Leading to α-Ketoamides

A metal-free oxidative coupling of methyl ketones and primary or secondary amines to alpha-ketoamides has been developed. Four intermediates, alpha-iodoketone, alpha-aminoketone, iminium intermediate, and alpha-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.