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

Chem Commun (Camb). 2022 Dec 1;58(96):13345-13348. 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.

MeSH terms

  • Amination
  • Amines*
  • Catalysis
  • Electricity*
  • Imines

Substances

  • Amines
  • Imines