Electricity-driven three-component reductive coupling reaction for the synthesis of diarylmethylamine?

Chemical Communications Pub Date: 2022-11-08 DOI: 10.1039/D2CC05330F

Abstract

A three-component reductive coupling reaction of aldehydes, amines and cyanopyridines under electrochemical conditions has been developed. The in situ generated imine and cyanopyridine simultaneously undergo single-electron reduction at the cathode, and afford diarylmethylamines through radical coupling without the participation of reducing agents. The one-pot electrolysis method can modularly obtain various secondary and tertiary amines and exhibits broad functional group compatibility. Mechanistic experiments verify the pivotal reduction step from imine to α-amino radical and reveal the key role of benzoic acid in reducing the reduction potential of imine and cyanopyridine.

Graphical abstract: Electricity-driven three-component reductive coupling reaction for the synthesis of diarylmethylamine
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