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 alpha-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 alpha-keto gem-diselenides showed excellent antimicrobial activity against Candida albicans, which can be identified as the lead compounds for further exploration.

Automated summary

We report a metal-free, electrochemical method for the highly selective synthesis of valuable organoselenium compounds. By coupling alpha-keto sulfoxonium ylides with diselenides, the electrochemical selenylation reaction exhibits broad scope and functional group tolerance. Mechanistic studies reveal that the key C-Se bond is constructed using n-Bu4NI as an electrolyte and catalyst in the electrosynthetic protocol. The resulting alpha-keto gem-diselenides show excellent antimicrobial activity against Candida albicans, suggesting their potential as lead compounds for further exploration.