Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines

Abstract

Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.

Keywords

• Electrocatalysis
• Cyclic amine
• β-Functionalization
• Sulfonylation
• Phosphonylation