Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing <i>C</i>-Vinyl Glycosides
Ming Li, Yi‐Feng Qiu, Cui‐Tian Wang, Xuesong Li, Wan‐Xu Wei, Yu‐Zhao Wang, Qiao-Fei Bao, Yanan Ding, Wei‐Yu Shi, Yong‐Min Liang
Abstract
A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.
Topics & Concepts
ChemistryGlycosylArylCatalysisOlefin fiberStyrenePalladiumBromideGlycosyl donorSelectivityVinyl bromideBromineCombinatorial chemistryHeck reactionMarkovnikov's ruleOrganic chemistryRegioselectivityAlkylPolymerCopolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques