Visible-Light-Mediated Synthesis of <i>C</i>-Alkyl Glycosides via Glycosyl Radical Addition and Aryl Migration
Rui-Qiang Jiao, Yanan Ding, Ming Li, Wei‐Yu Shi, Xi Chen, Zhe Zhang, Wan‐Xu Wei, Xuesong Li, Xiao-Ping Gong, Yu‐Yong Luan, Xue‐Yuan Liu, Yong‐Min Liang
Abstract
A visible-light-induced glycoarylation of activated olefins has been accomplished. Glycosyl radicals are generated via radical transfer strategies between (TMS) 3 SiOH and glycosyl bromides. Subsequent radical translocation and rapid 1,4-aryl migration form β-sugar amide derivatives, and eight types of sugars are compatible with this reaction. Further, the cascade reaction produced a quaternary carbon center with good functional group adaptability and high regioselectivity in mild conditions.
Topics & Concepts
ChemistryGlycosylAlkylArylRadicalRegioselectivityAmideFunctional groupGlycosyl donorCascade reactionOrganic chemistryCatalysisPolymerCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis TechniquesChemical Synthesis and Analysis