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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Veröffentlicht in:	Journal of organic chemistry 2023-05, Vol.88 (9), p.5572-5585
Hauptverfasser:	Xu, Zhongnan, Yao, Jiwen, Zhong, Kaihui, Lin, Shuimu, Hu, Xinwei, Ruan, Zhixiong
Format:	Artikel
Sprache:	eng
Schlagworte:	Anti-Infective Agents - pharmacology Fungi Pharmaceutical Preparations
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container_title	Journal of organic chemistry
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creator	Xu, Zhongnan Yao, Jiwen Zhong, Kaihui Lin, Shuimu Hu, Xinwei Ruan, Zhixiong
description	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.
doi_str_mv	10.1021/acs.joc.3c00091
format	Article
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subjects	Anti-Infective Agents - pharmacology Fungi Pharmaceutical Preparations
title	Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of gem-Diselenides as Antimicrobials against Fungi
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