The palladium (I1) complexes of the olefins ethene, propene, and 1-hexene reacted with 1- lithioindole to produce N-alkylated indoles exclusively. Attempts to perform this N-alkylation intramolecularly (to form tricyclic material from 2-allylskatole) failed. Anilines with dienic side chains in the 2-position were subjected to Pd (I1)-assisted cyclization conditions in attempts to induce polycyclization. However, only monocyclization was observed.