Sonogashira
SMARTS: [#6;$(C=C-[#6]),$(c:c):1][Br,I].[CH1;$(C#CC):2]>>[#6:1][C:2]
Conditions
Reactant 1: organohalide.
Reactant 2: alkyne.
R1: aryl, alkyl. R2: H, any carbon. X: Br, I.
References
Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Letters 1975, 16, 4467–4470
Other sources
Organic chemistry
Wikipedia