Suzuki-Miyaura reaction
Abstract
The Suzuki-Miyaura coupling is a palladium-catalyzed cross-coupling reaction that involves an organoboron compound, a base (NaOH, K2CO3...) and an organic halide (R1-X, where R = aryl, vinyl or alkyl, and X = I, Br or Cl) to form a new carbon-carbon bond.
Keywords
Aryl halide, Vinyl halide, Alkyl halide, Organoboron, Cross coupling
Category
Organometallic catalysis
Mechanism
The first step is the oxidative addition of the organic halide to the palladium(0) center. Next, the halide ligand is exchanged with a hydroxide from sodium hydroxide (NaOH) in our example, generating a palladium hydroxide intermediate(II). This species then undergoes transmetallation with the boronate complex. The boronate is formed when the boronic acid reacts with a NaOH. Finally, reductive elimination produces the desired product and regenerates the palladium(0) catalyst.
Recent review
Beletskaya, I. P.; Alonso, F.; Tyurin, V. The Suzuki-Miyaura reaction after the Nobel prize. Coord. Chem. Rev. 2019, 385, 137-173.