Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes
Wei‐Tai Fan, Yuting Li, Dongjie Wang, Shun‐Jun Ji, Yingsheng Zhao
Abstract
Direct functionalization of a C–H bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C–H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only activated the aromatic ring but also induced para selectivity due to the influence of ligand sterics.
Topics & Concepts
ChemistrySelectivityCatalysisPorphyrinSteric effectsCombinatorial chemistryLigand (biochemistry)Surface modificationRing (chemistry)StereochemistryOrganic chemistryReceptorBiochemistryPhysical chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsInorganic Fluorides and Related Compounds