Radical-mediated silyl- and germyldesulfonylation of vinyl and (alpha-fluoro)vinyl sulfones: application of tris(trimethylsilyl)silanes and tris(trimethylsilyl)germanes in Pd-catalyzed couplings

Org Lett. 2004 Jun 10;6(12):2047-9. doi: 10.1021/ol049312n.

Abstract

[reaction: see text] Radical-mediated silyl- and germyldesulfonylations of various vinyl and (alpha-fluoro)vinyl sulfones with tris(trimethylsilyl)silane and germanium hydrides provide access to vinyl and (alpha-fluoro)vinyl silanes and germanes. Upon oxidative treatment with hydrogen peroxide in basic aqueous solution, the vinyl tris(trimethylsilyl)silanes and -germanes undergo Pd-catalyzed cross-couplings with aryl halides.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Germanium / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Silanes / chemical synthesis*
  • Sulfones* / chemical synthesis
  • Sulfones* / chemistry
  • Trimethylsilyl Compounds / chemical synthesis*
  • Vinyl Compounds* / chemical synthesis
  • Vinyl Compounds* / chemistry

Substances

  • Silanes
  • Sulfones
  • Trimethylsilyl Compounds
  • Vinyl Compounds
  • Germanium
  • Palladium