Cobalt-catalyzed cross-coupling between in situ prepared arylzinc halides and 2-chloropyrimidine or 2-chloropyrazine

J Org Chem. 2009 Apr 17;74(8):3221-4. doi: 10.1021/jo900240d.

Abstract

A cobalt-catalyzed cross-coupling of aryl halides with 2-chloropyrimidines or 2-chloropyrazines is reported in satisfactory to high yields. The key step of this procedure is the formation of aromatic organozinc reagents and their coupling with 2-chlorodiazines using the same cobalt halide as catalyst and Zn dust under mild reaction conditions. This new cobalt-catalyzed coupling reaction represents a practical and interesting alternative to previously known methods for the synthesis of 2-aryldiazines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cobalt / chemistry*
  • Cross-Linking Reagents
  • Hydrocarbons, Chlorinated / chemistry*
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry*
  • Structure-Activity Relationship
  • Zinc Compounds / chemical synthesis*
  • Zinc Compounds / chemistry*

Substances

  • 2-chloropyrazine
  • 2-chloropyrimidine
  • Cross-Linking Reagents
  • Hydrocarbons, Chlorinated
  • Indicators and Reagents
  • Pyrazines
  • Pyrimidines
  • Zinc Compounds
  • Cobalt