Cathodic N–O Bond Cleavage of N-Alkoxy Amide

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 ge...

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Bibliographic Details
Published inDenki kagaku oyobi kōgyō butsuri kagaku Vol. 91; no. 11; p. 112005
Main Authors SATO, Eisuke, OGITA, Sayaka, MITSUDO, Koichi, SUGA, Seiji
Format Journal Article
LanguageEnglish
Japanese
Published Tokyo The Electrochemical Society of Japan 28.11.2023
Japan Science and Technology Agency
Subjects
Amides
Cathodic Reduction
Chemical reduction
Cleavage
Density functional theory
Direct reduction
N-Alkoxy Amide
Weinreb Amide
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Summary: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.
ISSN:1344-3542
2186-2451
DOI:10.5796/electrochemistry.23-67079