Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids

The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.

Automated summary

A novel electrochemical reductive arylation method was developed for the efficient synthesis of various diarylamines without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell, and several derivatization reactions were successfully carried out. Cyclic voltammetry experiments and mechanism studies revealed the roles of acetonitrile, formic acid, and triethyl phosphite in promoting this reductive arylation transformation.