Electrophotocatalytic C−H Heterofunctionalization of Arenes

He Huang; Tristan H. Lambert

doi:10.1002/anie.202100222

Electrophotocatalytic C−H Heterofunctionalization of Arenes

He Huang
, Tristan H. Lambert^*

^*Corresponding author for this work

Cornell University

Research output: Contribution to journal › Article › peer-review

108 Citations (Scopus)

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.

Original language	English
Pages (from-to)	11163-11167
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	20
DOIs	https://doi.org/10.1002/anie.202100222
Publication status	Published - 10 May 2021
Externally published	Yes

Keywords

alkoxylation
amination
electrophotocatalysis
hydroxylation
photochemistry

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10.1002/anie.202100222

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title = "Electrophotocatalytic C−H Heterofunctionalization of Arenes",

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",

author = "He Huang and Lambert, \{Tristan H.\}",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2021",

month = may,

day = "10",

doi = "10.1002/anie.202100222",

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T1 - Electrophotocatalytic C−H Heterofunctionalization of Arenes

AU - Huang, He

AU - Lambert, Tristan H.

PY - 2021/5/10

Y1 - 2021/5/10

N2 - 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.

AB - 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.

KW - alkoxylation

KW - amination

KW - electrophotocatalysis

KW - hydroxylation

KW - photochemistry

UR - https://www.scopus.com/pages/publications/85104127997

U2 - 10.1002/anie.202100222

DO - 10.1002/anie.202100222

M3 - Article

C2 - 33661562

AN - SCOPUS:85104127997

SN - 1433-7851

VL - 60

SP - 11163

EP - 11167

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

Electrophotocatalytic C−H Heterofunctionalization of Arenes

Abstract

Keywords

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