4.8 Article

Electrophotocatalytic C-H Heterofunctionalization of Arenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 20, Pages 11163-11167

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202100222

Keywords

alkoxylation; amination; electrophotocatalysis; hydroxylation; photochemistry

Funding

  1. NIGMS [R35 GM127135]

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

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