Abstract Pd (II) catalyzed reaction of N-carbomethoxy-2-alkynylanilines with allyl chlorides produces 2-alkyl-3-allyl-N-carbomethoxyindoles in the presence of oxirances; Aminopalladation of a N-carbomethoxy-2-alkynylaniline gives 3-(N-carbomethoxyindolyl) palladium intermediate, which regioselectively attacks on the γ position of chlorides to give 3- allyl-2-alkylindoles with concurrent regeneration of Pd (II) catalyst.