Photoredox‐Catalyzed Functionalization of Alkenes with Thiourea Dioxide: Construction of Alkyl Sulfones or Sulfonamides
Yuewen Li, Jin‐Biao Liu, Fu‐Sheng He, Jie Wu
Abstract
Summary of main observation and conclusion Sulfonylation of alkenes through photoredox‐catalyzed functionalization of alkenes with thiourea dioxide under visible‐light irradiation is achieved. The reaction of alkenes, thiourea dioxide and electrophiles provides a green and efficient access to alkyl sulfones and sulfonamides. A broad reaction scope is presented with good functional group compatibility and excellent regioselectivity. A plausible mechanism involving a radical addition process with sulfur dioxide radical anion (SO 2 ‐ ) derived from the oxidation of sulfur dioxide anion (SO 2 2– ) is proposed, which is supported by fluorescence quenching experiments.
Topics & Concepts
ChemistryPhotoredox catalysisRegioselectivitySurface modificationAlkylElectrophileThioureaSulfur dioxidePhotochemistryCatalysisQuenching (fluorescence)Organic chemistryCombinatorial chemistryFluorescencePhotocatalysisQuantum mechanicsPhysical chemistryPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions