Electrochemically Mediated S-Glycosylation of 1-Thiosugars with Xanthene Derivatives
Ruiqi Wang, Qinghui Jiang, Huixiang Wang, Xiaowei Zhang, Nan Yan
Abstract
An efficient electrochemical dehydrogenative cross-coupling of benzylic C-H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various glycosylated xanthene derivatives with up to 91% yield. This current electrooxidative reaction is characterized by high atom economy, high efficiency, mild reaction conditions, being environmentally benign, and excellent functional group tolerance. Moreover, preliminary mechanistic investigations reveal that the reaction involves a free radical process.
Topics & Concepts
XantheneChemistryGlycosylationYield (engineering)Atom economyCombinatorial chemistryElectrochemistryFunctional groupCoupling reactionCatalysisPhotochemistryOrganic chemistryBiochemistryPhysical chemistryMetallurgyElectrodePolymerMaterials scienceSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods