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

Mechanism

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Related Compounds