Stille cross-coupling

Also known as: Kosugi-Migita-Stille coupling

Schematic of the Stille cross-coupling. Reagents: organohalide, organostannane, Palladium(0) catalyst, ligands. Product: coupled product. Comments: aryl, alkenyl, allyl, or acyl R groups.

The Stille cross-coupling reaction is the organic reaction of an organohalide with an organostannane com-pound to give the coupled product using a palladium catalyst. The mechanism begins with oxidative add-ition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organostannane then follows where the R group of the organostannane reagent 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 Stille cross-coupling. Stille Cross-Coupling Catalytic Cycle steps include: oxidative addition, transmetalation, and reductive elimination.

References:

1.
Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636–3638.
2.
Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992–4998.