A palladium-dihydroxyterphenylphosphine (DHTP) catalyst was successfully applied to the dearomative C3-arylation of tryptamine derivatives with aryl nonaflates. The intramolecular cyclization of the resulting 3,3-disubstituted indolenines afforded C3a-arylated pyrroloindolines in one pot. We postulate that the formation of complexes between the lithium salts of DHTP and the tryptamine derivative is the key to promoting selective arylation at the C3-position of the indole ring. Furthermore, reactions using homotryptamine derivatives successfully provided C4a-arylated pyridoindolines.