Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids
Dan Wang, Zhaohua Wan, Heng Zhang, Hesham Alhumade, Hong Yi, Aiwen Lei
Abstract
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.
Topics & Concepts
ChemistryAcetonitrileFormic acidCyclic voltammetryCombinatorial chemistryElectrochemistryDerivatizationFlow chemistryOrganic synthesisCatalysisReductive eliminationTransition metalOrganic chemistryHigh-performance liquid chromatographyPhysical chemistryElectrodeRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods