Palladium-Catalyzed <i>ortho</i>-C–H Glycosylation/<i>ipso</i>-Alkenylation of Aryl Iodides
Yanan Ding, Wei‐Yu Shi, Ce Liu, Nian Zheng, Ming Li, Yang An, Zhe Zhang, Cui‐Tian Wang, Bo‐Sheng Zhang, Yong‐Min Liang
Abstract
This report describes the first example of palladium-catalyzed ortho-C–H glycosylation/ipso-alkenylation of aryl iodides, and the easily accessible glycosyl chlorides are used as a glycosylation reagent. The reaction is compatible with the functional groups of the substrates, and a series of C-aryl glycosides have been synthesized in good to excellent yield and with excellent diastereoselectivity. It is found that a cheap 5-norbornene-2-carbonitrile as a transient mediator can effectively promote this reaction. In addition, ipso-arylation and cyanation were also realized by the strategy.
Topics & Concepts
GlycosylationArylPalladiumChemistryNorborneneReagentGlycosylCatalysisYield (engineering)Combinatorial chemistryGlycosideOrganic chemistryMedicinal chemistryMaterials sciencePolymerMonomerAlkylMetallurgyBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthesis of Indole Derivatives