Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides

J Am Chem Soc. 2009 Jun 10;131(22):7532-3. doi: 10.1021/ja902046m.

Abstract

An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired beta-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp(3))-C(sp(2)) bond formation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Bromobenzenes / chemistry*
  • Catalysis
  • Chlorobenzenes / chemistry*
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry
  • Zinc / chemistry*

Substances

  • Benzene Derivatives
  • Bromobenzenes
  • Chlorobenzenes
  • Organometallic Compounds
  • Palladium
  • Zinc