Indole
SMARTS: [*;Br,I;$(*c1ccccc1)]-[c:1]:[c:2]-[NH2:3].[CH1:5]#[C;$(C-[#6]):4]>>[c:1]1:[c:2]-[N:3]-[C:4]=[C:5]-1
Conditions
Reactant 1: bromide and iodide allowed.
Reactant 2: alkyne.
R1: ar, alkyl.
References
B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett., 2006, 8, 3271-3274.
Other sources
Organic chemistry