Heating a DMA/pivalic acid (v/v= 4/1) solution of diversely substituted 6-(phenylamino) hex-2- ynoates in the presence of a catalytic amount of Pd (OAc) 2 under oxygen atmosphere afforded pyrrolo [1, 2-a] indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C–H activation and reductive elimination was proposed to account for the observed bis-cyclization.