Thioglycoside functionalization via chemoselective phosphine acceleration of a photocatalytic thiol–ene reaction

Abstract

Thioglycosides are enzymatically stable carbohydrate variants used in biotechnology as probes and investigational drugs. To date, harsh activation conditions limit the scope of thiol–ene sugar ligations. Here, we show that phosphines act as a photoredox mediator to accelerate radical thiol–ene reactions between thiosugars and olefins, enabling mild visible light-driven, ambient, and fully aqueous conditions.