title: Visible light mediated activation and O-glycosylation of thioglycosides.
abstract: Visible light catalysis allows the efficient construction of single electron transfer (SET) redox cycles that result in minimal formation of byproducts and proceed under exogenous control of a removable light source. The O-glycosylation of thioglycosides via visible light photoredox chemistry is reported. Mechanistic studies show that the reaction is fully light responsive and support a mechanism involving decomposition of an oxidatively generated sulfur radical cation and propagation via reduction of the thiol side product.
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA.
authors.forename: Walter J
authors.initials: WJ
authors.lastname: Wever
authors.forename: Maris A
authors.initials: MA
authors.lastname: Cinelli
authors.forename: Albert A
authors.initials: AA
authors.lastname: Bowers
mesh_terms: D002384:Catalysis; D004579:Electron Transport; D006031:Glycosylation; D008027:Light; D015394:Molecular Structure; D010084:Oxidation-Reduction / Q000528:radiation effects; D055668:Photochemical Processes; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D013438:Sulfhydryl Compounds; D013865:Thioglycosides