Negishi reaction
Abstract
Negishi reaction is a palladium or nickel catalyzed cross-coupling reaction between an aryl halide, vinyl halide or alkyl halide (R1-X, where X = I, Br or Cl) and an organozinc (R2-ZnY, where Y = I, Br or Cl).
Keywords
Aryl halide, Vinyl halide, Alkyl halide, Organozinc, Cross-coupling
Category
Organometallic catalysis
Mechanism
The catalytic reaction starts with the oxidative addition of the organic halide (here an aryl halide) to the metal(0) center. The aryl-metal(II) complex undergoes transmetallation with an organozinc reagent, transferring the organic group from zinc to the metal center. Finally the reductive elimination results in the formation of the desired product and regenerates the catalyst.
Recent review
Muzammil, Z.; Zahoor, A. F.; Parveen, B.; Javed, S.; Akhtar, R.; Tabassum, S. Recent developments in the chemistry of Negishi coupling: A review. Chem. Pap. 2024, 78, 3399-3430.