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Electrochemical Approach to Amide Bond Formation

Sofia Strekalova, A. M. Kononov, V. I. Morozov, Olga B. Babaeva, Е. Л. Гаврилова, Yulia H. Budnikova

2023Advanced Synthesis & Catalysis24 citationsDOI

Abstract

Abstract Electrochemical amidation of the C( sp 2 )−H and C( sp 3 )−H bonds of broad spectrum of arenes toward the direct synthesis of anilides and N ‐benzylamides under mild conditions (room temperature, ambient pressure) in the absence of metal catalyst and external oxidizing agents using nitriles RCN (R=Me, Et) as amide source is described. This electrochemical approach features moderate to high yields, a broad scope of arenes with different functional groups and is amenable to gram scale synthesis. The key role of the hydroxyl radical as inductor generated during the oxidation of water and fixed by a spin trap in EPR experiment has been established.

Topics & Concepts

ChemistryElectrochemistryAmideOxidizing agentCatalysisCombinatorial chemistryHydrogen bondPhotochemistryOrganic chemistryMoleculePhysical chemistryElectrodeRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
Electrochemical Approach to Amide Bond Formation | Litcius