Deoxygenative arylation of secondary amides by merging iridium catalysis with electrochemical radical cross-coupling

Abstract

Given the natural abundance and industrial accessibility, inert amides have gained considerable attention in homologous amine synthesis and the development of novel catalytic strategies for their deoxygenative functionalization is highly desirable. Although organic electrosynthesis has become a revolutionary research area by virtue of its sustainability and atom economy, the combination of amide reduction with an electrochemical process in value-added amine synthesis is still undeveloped. Herein, a strategy merging iridium-catalyzed activation of amides with electrochemical radical generation to access deoxygenative arylation of secondary amides is developed. This methodology features broad substrate scope, mild reaction conditions, and operational simplicity, giving corresponding benzylic amines with high efficiency. Notably, the successful application of the electrochemical method in the deoxygenative functionalization of amides would provide an efficient strategy for quick access to value-added amines from inert amides.