Palladium‐Catalyzed Intermolecular Dicarbofunctionalization of Unactivated Alkenes: Synthesis of Fluoroalkylated Heterocycles with All‐Carbon Quaternary Centers
Jiajia Cheng, Huali Zhang, Jinliang Lv, Jinhua Zheng
Abstract
Abstract The redox‐neutral palladium‐catalyzed dicarbofunctionalization of unactivated alkenes with a variety of functionalized difluoromethyl and perfluoroalkyl halide is presented here. This transformation proceeds smoothly at low temperatures and enables the assembly of diversified fluoroalkylated pyrrolo[1,2‐a]indole derivatives with one all‐carbon quaternary center in high regioselectivity. Mechanistic studies suggested an operative radical mechanism and the initiation of the inner‐sphere single electron transfer between a dual phosphine ligand‐coordinated palladium(0) species and perfluoroalkyl halides.
Topics & Concepts
ChemistryPalladiumRegioselectivityPhosphineHalideCatalysisLigand (biochemistry)Intermolecular forceCombinatorial chemistryOrganic chemistryMoleculeBiochemistryReceptorFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions