Ruthenium-Catalyzed Pyridine-Directed Aryl C–H Glycosylation with Glycosyl Chlorides
Shaokun Cai, Qikai Sun, Quanquan Wang, Gang He, Gong Chen
Abstract
Metal-catalyzed C–H glycosylation reactions with glycosyl chloride donors have emerged as a useful strategy for the synthesis of C-glycosides. Previously, palladium and nickel complexes were reported to catalyze C–H glycosylation reactions using amide-linked bidentate auxiliaries. Herein, a ruthenium-catalyzed ortho C–H glycosylation reaction of arenes with various glycosyl chloride donors using a monodentate pyridine directing group is developed. Preliminary mechanistic studies indicated that two-electron oxidative addition and reductive elimination of ruthenocycle intermediate led to the glycosylation products.
Topics & Concepts
ChemistryGlycosylationGlycosylPyridineArylCatalysisRutheniumAmideMedicinal chemistryOxidative additionPalladiumDenticityCombinatorial chemistryStereochemistryOrganic chemistryMetalAlkylBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques