An electrochemical nickel-catalyzed arylation of 3-amino-6-chloropyridazines

J Org Chem. 2013 Jan 18;78(2):370-9. doi: 10.1021/jo3022428. Epub 2013 Jan 4.

Abstract

3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Electrochemical Techniques
  • Molecular Structure
  • Nickel / chemistry*
  • Pyridazines / chemical synthesis*
  • Pyridazines / chemistry*

Substances

  • Cross-Linking Reagents
  • Pyridazines
  • Nickel