α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of N-Allylimines to Pyrroles

Abstract

We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through R-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization.

Publication
Chen, Z.; Lu, B.; Ding, Z.; Gao, K.; Yoshikai, N. Org. Lett. 2013, 15, 1966-1969.