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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
- 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.
- Fukuyama Coupling
- Hiyama Coupling
- Kumada Coupling
- Suzuki Cross-Coupling
- Stille Cross-Coupling
- Catalytic Pd
- Catalytic Ni