Highly regioselective and stereoselective synthesis of C-Aryl glycosides <i>via</i> nickel-catalyzed <i>ortho</i>-C–H glycosylation of 8-aminoquinoline benzamides
Wei‐Yu Shi, Yanan Ding, Nian Zheng, Xue‐Ya Gou, Zhe Zhang, Xi Chen, Yu‐Yong Luan, Zhi‐Jie Niu, Yong‐Min Liang
Abstract
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzed ortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
Topics & Concepts
RegioselectivityStereoselectivityChemistryGlycosylationArylSelectivityCatalysisNickelCombinatorial chemistryGlycosideStereochemistryOrganic chemistryAlkylBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsPneumocystis jirovecii pneumonia detection and treatment