Suzuki cross-coupling

Also known as: Suzuki-Miyaura cross-coupling

Schematic of the Suzuki cross-coupling. Reagents: organohalide, organoborane, Palladium(0) catalyst, ligands, base. Product: coupled product. Comments: aryl, alkenyl, alkyl, or allyl R groups.

The Suzuki cross-coupling reaction is the organic reaction of an organohalide with an organoborane to give the coupled product using a palladium catalyst and base. The mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. A molecule of the hydroxide or alkoxide base then replaces the halide on the palladium complex, while another adds to the organoborane to form a borate regent making its R group more nucleophilic. Transmetalation with the borate then follows where its R group replaces the halide anion on the palladium complex. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1][2]

Mechanism

Mechanism of the Suzuki cross-coupling. Suzuki Cross-Coupling Catalytic Cycle steps include: oxidative addition, transmetalation, and reductive elimination.

References:

1.
Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Letters 1979, 20, 3437–3440.