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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
- King, A. O.; Okukado, N.; Negishi, E. Highly General Stereo-, Regio-, and Chemo-Selective Synthesis of Terminal and Internal Conjugated Enynes by the Pd-Catalysed Reaction of Alkynylzinc Reagents with Alkenyl Halide. J. Chem. Soc., Chem. Commun. 1977, No. 19, 683-684.
- 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.
- Fukuyama Coupling
- Hiyama Coupling
- Kumada Coupling
- Suzuki Cross-Coupling
- Stille Cross-Coupling
- Catalytic Pd
- Catalytic Ni