title: General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation.
abstract: Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd(0) utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.
authors.affiliation: Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102 (USA).
authors.forename: Guangrong
authors.initials: G
authors.lastname: Meng
authors.affiliation: Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102 (USA). michal.szostak@rutgers.edu.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
keywords: Heck reaction; NC activation; amide bonds; base-free Heck reaction; twisted amides