Photochemical “Cut and Sew” Transformations of Ethynylbenziodoxolone Reagents and Diazo Compounds
Mengting Cao, Yikun Ren, Ruoyu Zhang, Huayan Xu, Huayan Xu, Pengfei Cheng, Hao Xu, Hao Xu, Yuanqing Xu, Pan Li
Abstract
Herein, we disclose a visible-light-induced oxy-alkynylation of diazo compounds with ethynylbenziodoxolones. The efficient protocol provides a mild and metal-free methodology to synthesize propargylic esters in moderate to good yields. Notably, this metal-free carbene transfer reaction appears to involve an oxonium ylide intermediate, followed by intramolecular ligand exchange and reductive elimination.
Topics & Concepts
DiazoChemistryOxonium ionIntramolecular forceYlideReagentCarbeneLigand (biochemistry)Combinatorial chemistryMetalPhotochemistryStereochemistryOrganic chemistryCatalysisReceptorBiochemistryIonCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions