Palladium-Catalyzed Synthesis of (Hetero)Aryl Alkyl Sulfones from (Hetero)Aryl Boronic Acids, Unactivated Alkyl Halides, and Potassium Metabisulfite

Angew Chem Int Ed Engl. 2015 Nov 9;54(46):13571-5. doi: 10.1002/anie.201505918. Epub 2015 Sep 18.

Abstract

A palladium-catalyzed one-step synthesis of (hetero)aryl alkyl sulfones from (hetero)arylboronic acids, potassium metabisulfite, and unactivated or activated alkylhalides is described. This transformation is of broad scope, occurs under mild conditions, and employs readily available reactants. A stoichiometric experiment has led to the isolation of a catalytically active dimeric palladium sulfinate complex, which was characterized by X-ray diffraction analysis.

Keywords: alkylation; boronic acids; homogeneous catalysis; palladium; sulfones.

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Hydrocarbons, Halogenated / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Sulfites / chemistry*
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry

Substances

  • Boronic Acids
  • Hydrocarbons, Halogenated
  • Organometallic Compounds
  • Sulfites
  • Sulfones
  • Palladium
  • potassium metabisulfite