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


Top Citations

Original Paper

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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