title: Thioetherification via Photoredox/Nickel Dual Catalysis.
abstract: Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aromatic bromides to furnish thioethers. The serendipitous discovery of this reaction and its utilization for the thioetherification of various aryl and heteroaryl bromides with a diverse array of thiols is described. The S-H selective H atom abstraction event enables a wide range of functional groups, including those bearing protic moieties, to be tolerated.
authors: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors: Matthieu
authors: M
authors: Jouffroy
authors: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors: Christopher B
authors: CB
authors: Kelly
authors: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors: Gary A
authors: GA
authors: Molander
mesh_terms: D002384:Catalysis; D004951:Esterification; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D017640:Silicates / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry
chemical_list: D006842:Hydrocarbons, Brominated; D017640:Silicates; D013440:Sulfides; D009532:Nickel