Using the Thiyl Radical for Aliphatic Hydrogen‐Atom Transfer: Thiolation of Unactivated C−H Bonds
Liubov I. Panferova, Mikhail O. Zubkov, Vladimir A. Kokorekin, Vitalij V. Levin, Alexander D. Dilman
Abstract
A metal- and catalyst-free thiyl-radical-mediated activation of alkanes is described. Tetrafluoropyridinyl disulfide is used to perform thiolation of the C-H bonds under irradiation with 400 nm light-emitting diodes. The key C-H activation step is believed to proceed via hydrogen-atom abstraction effected by the fluorinated thiyl radical. Secondary, tertiary, and heteroatom-substituted C-H bonds can be involved in the thiolation reaction. The resulting sulfides have wide potential as photoredox-active radical precursors in reactions with alkenes and heteroarenes.
Topics & Concepts
ChemistryPhotochemistryHydrogen atom abstractionDisulfide bondCatalysisHeteroatomHydrogen atomHydrogen bondHydrogenMoleculeOrganic chemistryAlkylBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques