Facilitating Ir-Catalyzed C–H Alkynylation with Electrochemistry: Anodic Oxidation-Induced Reductive Elimination
Xiaohan Ye, Chenhuan Wang, Shuyao Zhang, Jingwen Wei, Chuan Shan, Łukasz Wojtas, Yan Xie, Xiaodong Shi
Abstract
An electrochemical approach in promoting directed C–H alkynylation with terminal alkyne via iridium catalysis is reported. This work employed anodic oxidation of Ir(III) intermediate (characterized by X-ray crystallography) to promote reductive elimination, giving the desired coupling products in good yields (up to 95%) without the addition of any other external oxidants. This transformation is suitable for various directing groups with H2 as the only byproduct, which warrants a high atom economy and practical oxidative C–C bond formation under mild conditions.
Topics & Concepts
CatalysisIridiumElectrochemistryAlkyneChemistryReductive eliminationAlkynylationAnodeCombinatorial chemistryRedoxOxidative coupling of methanePhotochemistryMedicinal chemistryInorganic chemistryOrganic chemistryElectrodePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions