An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions

An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bioactive molecules and gram-scale transformatio...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-01, Vol.24 (1), p.13-135
Main Authors: Fu, Zhengjiang, Yin, Jian, He, Dongdong, Yi, Xuezheng, Guo, Shengmei, Cai, Hu
Format: Article
Language:English
Subjects:
Anodizing
Catalysts
Chemical synthesis
Electrochemistry
Green chemistry
Oxidants
Oxidation
Oxidizing agents
Substrates
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Summary:An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bioactive molecules and gram-scale transformation have been performed to highlight the synthetic utility of the protocol. CV (cyclic voltammetry) experiment indicates that anodic oxidation of diselenide occurs prior to that of the arylboronic acid substrate under the standard conditions. An electrochemical deborylative selenylation of arylboronic acids has been developed to produce aryl selenoethers in good yields, whose practicability has been highlighted through the synthesis of bioactive molecules and gram-scale preparation.
ISSN:1463-9262
1463-9270
DOI:10.1039/d1gc02962b