Azoliums and Ag(I)‐N‐Heterocyclic Carbene Thioglycosides: Synthesis, Reactivity and Bioactivity

Abstract A versatile protocol for the synthesis of azolium thioglycosides is reported. This protocol is based on a PdG3‐catalyzed Migita cross‐coupling between p‐di‐iodo azoliums and protected or unprotected β‐1‐thioglucose partners. Moreover, a solvent‐free mechanochemistry approach was developed as a unique access to the corresponding Ag(I)‐N‐heterocyclic carbene thioglycosides. Finally, chemical reactivity and antiproliferative bioactivity were examined with azoliums and Ag(I)‐NHC thioglycosides. This study demonstrates a promising potential of these newly synthesized carbohydrate‐based N‐heterocyclic derivatives.