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

Guangrong Meng, Michal Szostak

Research output: Contribution to journalArticlepeer-review

263 Scopus citations

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 Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

Original languageEnglish (US)
Pages (from-to)14518-14522
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number48
DOIs
StatePublished - Nov 23 2015

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry

Keywords

  • Heck reaction
  • N-C activation
  • amide bonds
  • base-free Heck reaction
  • twisted amides

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