Visible-Light-Induced PhI(OAc)<sub>2</sub>-Mediated Alkylation of Heteroarenes with Simple Alkanes and Ethers
Lusina Mantry, Parthasarathy Gandeepan
Abstract
The direct alkylation of heteroarenes with alkanes has been successfully achieved through visible-light-induced hypervalent iodine-mediated C-H functionalization of both coupling partners at ambient temperatures. This reaction proceeds via the in situ generation of nucleophilic alkyl radicals from alkanes through hydrogen atom transfer (HAT), followed by a Minisci-type reaction with heteroarenes. These mild reaction conditions have demonstrated their suitability for the alkylation of a wide range of heterocycles, including azoles, pyridines, quinolines, isoquinolines, and quinoxalinones.
Topics & Concepts
AlkylationHypervalent moleculeChemistryNucleophileAlkylRadicalPhotochemistryVisible spectrumHydrogen atomSurface modificationMedicinal chemistryIodineOrganic chemistryCatalysisMaterials sciencePhysical chemistryOptoelectronicsRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods