Cathodic N–O Bond Cleavage of N-Alkoxy Amide

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.

Keywords

• n-alkoxy amide
• cathodic reduction
• weinreb amide