Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling of α-keto sulfoxonium ylides with diselenides. The versatility of the electrochemical manifo...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-05, Vol.88 (9), p.5572-5585
Main Authors: Xu, Zhongnan, Yao, Jiwen, Zhong, Kaihui, Lin, Shuimu, Hu, Xinwei, Ruan, Zhixiong
Format: Article
Language:English
Subjects:
Anti-Infective Agents - pharmacology
Fungi
Pharmaceutical Preparations
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Summary:Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of gem-diselenides through the coupling of α-keto sulfoxonium ylides with diselenides. The versatility of the electrochemical manifold enabled the selenylation with ample scope and broad functional group tolerance, as well as setting the stage for modification of complex bioactive molecules. Detailed mechanistic studies revealed that the key C–Se bond was constructed using n-Bu4NI as an electrolyte and catalyst through the electrosynthetic protocol. Finally, the desired α-keto gem-diselenides showed excellent antimicrobial activity against Candida albicans, which can be identified as the lead compounds for further exploration.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00091