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Nickel‐Catalyzed Amide Bond Formation from Methyl Esters
Author(s) -
Ben Halima Taoufik,
MassonMakdissi Jeanne,
Newman Stephen G.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808560
Subject(s) - catalysis , chemistry , amide , stoichiometry , nickel , combinatorial chemistry , alcohol , coupling reaction , peptide bond , organic chemistry , enzyme
Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel‐catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid‐ and base‐mediated amidations, the reaction is proposed to proceed by a neutral cross coupling‐type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.