General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Guangrong Meng; Michal Szostak

doi:10.1002/anie.201507776

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Angew Chem Int Ed Engl. 2015 Nov 23;54(48):14518-22. doi: 10.1002/anie.201507776. Epub 2015 Oct 12.

Authors

Guangrong Meng¹, Michal Szostak²

Affiliations

¹ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102 (USA).
² Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102 (USA). michal.szostak@rutgers.edu.

PMID: 26458248
DOI: 10.1002/anie.201507776

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.

Keywords: Heck reaction; NC activation; amide bonds; base-free Heck reaction; twisted amides.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.