Cathodic N–O Bond Cleavage of N-Alkoxy Amide (Supporting Information)

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.

阴极还原高效断裂N-O键。在分隔电池中，Weinreb酰胺的简单阴极还原过程高效地提供了相应的酰胺，产率优良。循环伏安法实验及密度泛函理论计算表明，N-甲氧基酰胺的直接还原生成了甲氧基自由基和酰胺阴离子。由甲氧基自由基释放的甲醇将是断裂N-O键的驱动力。