Electrochemistry
Online ISSN : 2186-2451
Print ISSN : 1344-3542
ISSN-L : 1344-3542
Communications
Cathodic N–O Bond Cleavage of N-Alkoxy Amide
Eisuke SATO Sayaka OGITAKoichi MITSUDOSeiji SUGA
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2023 Volume 91 Issue 11 Pages 112005

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Abstract

Cathodic reduction efficiently cleaved N–O bonds. The simple cathodic reduction of Weinreb amides in a divided cell afforded the corresponding amide in good yields. Cyclic voltammetry experiments and density functional theory calculations suggested that the direct reduction of the N-methoxy amide generates the methoxy radical and amide anion. The release of methanol derived from methoxy radical would be the driving force of the N–O bond cleavage.

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© The Author(s) 2023. Published by ECSJ.

This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 License (CC BY, http://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse of the work in any medium provided the original work is properly cited. [DOI: 10.5796/electrochemistry.23-67079].
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