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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 2: 668 - 676

DOI: https://doi.org/10.6023/cjoc202403010

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Recent Advances toward Electro- and Electrophotochemical 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Catalyzed C—H/C—F Bonds Functionalization

  • Yongmei Li ,
  • Liangbo Sun ,
  • Kun Xu ,
  • Chengchu Zeng
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  • College of Chemistry and Life Science, Beijing University of Technology, Beijing 100124
*E-mail: ;

Received date: 2024-03-07

  Revised date: 2024-04-06

  Online published: 2024-05-11

Supported by

Beijing Natural Science Foundation(2222003); National Natural Science Foundation of China(22171015)

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Abstract

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a stoichiometric oxidant that is frequently used in traditional organic synthesis. Recently, the rapid development of organic electrochemistry has led to new advancements in DDQ-catalyzed C—H bonds functionalization. Moreover, the challenging C—H functionalization of electron-deficient arenes has been achieved through the merger of electrochemical DDQ catalysis and photoirradiation. In addition, the synthetic utility of electrophotochemical DDQ catalysis was further demonstrated by the nucleophilic aromatic substitution (SNAr) reaction of unactivated aryl fluorides. The recent developments in electro- and electrophotochemical DDQ-catalyzed C—H/C—F func- tionalizations with attention to their strategies and mechanistic insights are summarized. It is hoped that this not only deepens the understanding of this field, but also helps relevant researchers expand the application scope of DDQ catalysis.

Key words： 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ); electrocatalysis; organic electrosynthesis; electrophotocatalysis; C—H functionalization; C—F functionalization

Cite this article

Yongmei Li , Liangbo Sun , Kun Xu , Chengchu Zeng . Recent Advances toward Electro- and Electrophotochemical 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-Catalyzed C—H/C—F Bonds Functionalization[J]. Chinese Journal of Organic Chemistry, 2025 , 45(2) : 668 -676 . DOI: 10.6023/cjoc202403010

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