3 years ago

Nickel‐Catalyzed Amide Bond Formation from Methyl Esters

Stephen G. Newman, Jeanne Masson-Makdissi, Taoufik Ben Halima

Abstract

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.

Publisher URL: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201808560

DOI: 10.1002/anie.201808560

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