Negishi cross coupling

The use of organozinc reagents in the Negishi (Pd- or Ni-catalyzed) cross-coupling reaction with organohalides allows for a much greater functional group tolerance than in the Kumada cross-coupling reaction. Other benefits include high reactivity, high regio- and stereoselectivity, few side reactions and little toxicity. Unlike the addition of a base in the Suzuki cross-coupling reaction, additives are not required to boost reactivity. The mechanism follows the expected oxidative addition-reductive elimination cycle.

  • Reagents: Catalytic Palladium or Nickel, Ligand (PPh3, dppe, dppp, dppb, dppf, etc.)
  • Reactant: Organohalide, Organozinc
  • Product: Coupled product
  • Type of Reaction: C-C Cross-Coupling


Original Paper

Top Citations

  • An Extremely Active Catalyst for the Negishi Cross-Coupling Reaction. J. Am. Chem. Soc. 2004, 126 (40), 13028–13032.
  • Nickel-Catalysed Negishi Cross-Coupling Reactions: Scope and Mechanisms. Chem. Soc. Rev. 2009, 38 (6), 1598–1607.
  • Recent Developments in Negishi Cross-Coupling Reactions. ACS Catal. 2016,6 (3), 1540–1552.

Related Reactions

  • Fukuyama Coupling
  • Hiyama Coupling
  • Kumada Coupling
  • Suzuki Cross-Coupling
  • Stille Cross-Coupling

Related Compounds

  • Catalytic Pd
  • Catalytic Ni
By shuhan yang


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