Electrophotocatalytic C-H Heterofunctionalization of Arenes

Angew Chem Int Ed Engl. 2021 May 10;60(20):11163-11167. doi: 10.1002/anie.202100222. Epub 2021 Apr 12.

Abstract

The electrophotocatalytic heterofunctionalization of arenes is described. Using 2,3-dichloro-5,6-dicyanoquinone (DDQ) under a mild electrochemical potential with visible-light irradiation, arenes undergo oxidant-free hydroxylation, alkoxylation, and amination with high chemoselectivity. In addition to batch reactions, an electrophotocatalytic recirculating flow process is demonstrated, enabling the conversion of benzene to phenol on a gram scale.

Keywords: alkoxylation; amination; electrophotocatalysis; hydroxylation; photochemistry.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Benzene / chemistry
  • Benzoquinones / chemistry*
  • Catalysis
  • Electrochemical Techniques
  • Light
  • Molecular Structure
  • Phenols / chemical synthesis
  • Phenols / chemistry

Substances

  • Benzoquinones
  • Phenols
  • dichlorodicyanobenzoquinone
  • Benzene