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General Olefin Synthesis by the Palladium‐Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective NC Activation
Author(s) -
Meng Guangrong,
Szostak Michal
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507776
Subject(s) - chemistry , amide , catalysis , palladium , olefin fiber , steric effects , heck reaction , bond cleavage , decarbonylation , metal , combinatorial chemistry , medicinal chemistry , organic chemistry
Abstract Metal‐catalyzed reactions of amides proceeding via metal insertion into the NCO 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 NCO 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.