A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

The title compound, C15H11NO3S, was prepared by a facile synthetic approach. The N atom in the pyrrole ring of the indole moiety is pyramidal (bond-angle sum = 350.0°) and the phenyl ring of the phenylsulfonyl motif forms a dihedral angle of 76.24 (7)° with the mean plane of the indole ring system. In the crystal, C—H...O and C—H...π interactions link the molecules into a three-dimensional network.