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 accelerates radical thiol-ene reactions between thiosugars and olefins, enabling mild visible light-driven, ambient, and fully aqueous conditions.