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
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
ChemistryPhotochemistryCatalysisHydrogen atom abstractionHeteroatomDisulfide bondHydrogen atomPhotoredox catalysisHydrogen bondHydrogenMoleculePhotocatalysisOrganic chemistryAlkylBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques