关键词: 2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ), 电催化, 有机电合成, 光电催化, 碳-氢官能化, 碳-氟官能化

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 (S_NAr) 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