Electrochemical Selenylation of Sulfoxonium Ylides for the Synthesis of <i>gem</i>-Diselenides as Antimicrobials against Fungi

Abstract

Organoselenium compounds are important scaffolds in pharmaceutical molecules. Herein, we report metal-free, electrochemical, highly chemo- and regioselective synthesis of <i>gem</i>-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 <i>n</i>-Bu₄NI as an electrolyte and catalyst through the electrosynthetic protocol. Finally, the desired α-keto <i>gem</i>-diselenides showed excellent antimicrobial activity against <i>Candida albicans</i>, which can be identified as the lead compounds for further exploration.