Synthesis of sulfones from organozinc reagents, DABSO, and alkyl halides

Org Lett. 2014 Jan 3;16(1):154-7. doi: 10.1021/ol4031233. Epub 2013 Dec 5.

Abstract

Organozinc reagents react with the SO2 surrogate DABSO, and the resulting zinc sulfinate salts are alkylated in situ to afford sulfones. This transformation has a broad scope and is compatible with a wide range of structural motifs of medicinal chemistry relevance including nitrile, secondary carbamates, and nitrogen-containing heterocycles.

MeSH terms

  • Dapsone / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Sulfones / chemical synthesis*
  • Sulfones / chemistry
  • Zinc / chemistry*

Substances

  • Hydrocarbons, Halogenated
  • Organometallic Compounds
  • Sulfones
  • Dapsone
  • Zinc