Palladium-catalysed and base-dependent intra-molecular ipso-substitution and cyclisation strategies involving N-indolyl-substituted aryl-sulfonamides for the rapid construction of 2-aryl indole and indole-fused six-membered sultams are described. The Pd(OAc)2/Ph3P/Et3N combination delivers indolyl C2 arylated motifs via C(2)-N bond cleavage followed by C-C bond formation. In sharp contrast to this, the Pd(OAc)2/Ph3P/K2CO3 combination induced intramolecular-Heck cross-coupling affords polycyclic sultams exclusively. Thus, this strategy is completely additive-dependent. It also shows a broad substrate scope and delivers the corresponding products in good to high yields.