Stille
Additional step: reactant 1 has to be transformed into organostannane.
SMARTS: [#6;$(C=C-[#6]),$(c:c):1][Br,I].[Cl,Br,I][c:2]>>[c:2][#6:1]
Conditions
Reactant 1: organostannane.
Reactant 2: organohalide.
R1: aryl, vinyl. R2: any aromatic system. X: Cl, Br, I.
References
Milstein D., Stille J. K., J. Am. Chem. Soc., 1978, 100, 3636–3638.
Milstein D., Stille J. K., J. Am. Chem. Soc., 1979, 101, 4992–4998.
Other sources
Organic chemistry
Wikipedia