<scp>Pd‐Catalyzed <i>Ortho</i>‐Directed</scp> C—H Glycosylation of Arenes Using N‐linked Bidentate Auxiliaries
Quanquan Wang, Wanjun Zhu, Qikai Sun, Gang He, Gong Chen
Abstract
Main observation and conclusion A set of Pd‐catalyzed ortho ‐directed C—H glycosylation reactions with glycosyl chloride donors using various N‐linked bidentate auxiliaries has been developed for synthesis of C‐aryl glycosides. A broad range of pyranose and furanose moieties can be installed on the ortho position of arylamine, carbazole, indole and benzylamine type substrates in high yield and with high regio‐ and diastereoselectivity. These auxiliaries can be readily installed and removed under relatively mild conditions.
Topics & Concepts
ChemistryGlycosylationPyranoseFuranoseIndole testArylCatalysisYield (engineering)BenzylamineDenticityStereochemistryCarbazoleMedicinal chemistryCombinatorial chemistryOrganic chemistryRing (chemistry)MetalAlkylMaterials scienceMetallurgyBiochemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions