Iron-Catalyzed C(sp3)–H Alkylation through Ligand-to-Metal Charge Transfer
Tomislav Rovis, Yi Cheng Kang, Sean M. Treacy
Abstract
Abstract We report the FeCl3-catalyzed alkylation of nonactivated C(sp3)–H bonds. Photoinduced ligand-to-metal charge transfer at the iron center generates chlorine radicals that then preferentially abstract hydrogen atoms from electron-rich C(sp3)–H bonds distal to electron-withdrawing functional groups. The resultant alkyl radicals are trapped by electron-deficient olefins, and the catalytic cycle is closed by Fe(II) recombination and protodemetalation.
Topics & Concepts
ChemistryAlkylationCatalysisLigand (biochemistry)RadicalCatalytic cycleElectron transferMetalPhotochemistryAlkylMedicinal chemistryChlorineOrganic chemistryReceptorBiochemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsFluorine in Organic Chemistry