Stereocontrolled Synthesis of (Hetero)aryl/vinyl Selenoglycosides via a Silver-Catalyzed Aqueous C-Se Cross-Coupling Reaction.

Selenoglycosides display diverse biological activities, yet methods for their efficient and stereoselective syntheses remain underdeveloped. Herein, we present a silver-catalyzed C-Se cross-coupling strategy for the synthesis of a diverse array of (hetero)aryl/vinyl selenoglycosides from readily accessible glycosylselenosulfonates and boronic acids. This water-compatible protocol features mild conditions, outstanding stereoselectivity, and high functional group tolerance. Mechanistic studies revealed that this reaction follows a radical pathway. Notably, the efficient preparation of selenogliflozin analogues as potential SGLT2 inhibitors highlighted the synthetic practicality of this approach. Collectively, this work provides a practical platform for the rapid and stereoselective construction of Se-glycoside libraries for drug discovery.