Rh(II)-Catalyzed C-N Bond Formation Using Enynones and N-H Imines: An Approach to Diarylmethylamines

Abstract

A Rh(II)-catalyzed furyl carbene N-H insertion reaction involving an N-sp2-hybridized imine is described, which represents an atom-economical route by which to access diarylmethylamine derivatives with high efficiency and broad substrate scope. An unusual reaction mechanism is proposed, in which the rhodium catalyst plays a dual role in facilitating enynone cyclization via activation and enhancement of the nucleophilicity of the NH imine.