The Kumada cross-coupling reaction uses a palladium or nickel catalyst to couple an organohalide and a Grignard or organolithium reagent. The mechanism follows the expected oxidative addition-reductive elimination cycle.

  • Reagents: Catalytic Palladium or Nickel
  • Reactant: Organohalide, Organomagnesium or Organolithium
  • Product: Coupled Product
  • Type of Reaction: C-C Cross-Coupling

Lab Tips

  • Organolithium reagents are highly versatile as they can be prepared in multiple ways, including the direct lithiation of hydrocarbons.
  • Fast addition of the organolithium produces α-bromo alkenyllithiums that undergo rearrangement to give lithium acetylides, lowering yields.
  • No reagents should be added in excess and the Pd(0) catalyst should be clean to facilitate good yields.
  • Base-sensitive functional groups are not tolerated as they will react with the Grignard or organolithium reagent. Tolerance is improved with the Negishi cross-coupling, which uses organozinc reagents instead.
Kürti, L., Czakó, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis; Background and detailed mechanisms. Burlington, MA: Elsevier Academic Press.


Top Citations

Original Paper

Related Reactions

  • Grignard Reaction
  • Negishi Cross-Coupling
  • Suzuki Cross-Coupling
  • Stille Cross-Coupling

Related Compounds

  • Ni(dppp)Cl₂ (CAS 15629-92-2)
By shuhan yang


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