Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation

Abstract

A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of alpha-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.