AbstractAn efficient cascade methodology toward chemoselective synthesis of N‐fused heterocycles including 9H‐pyrrolo[1,2‐a]indole, 3H‐pyrrolo[1,2‐a]indole and 1H‐pyrrolo[1,2‐a]indole derivatives has been developed. This transformation proceeds via a silver(I) triflate‐catalyzed consecutive Friedel–Crafts reaction/NC bond formation sequence between readily available propargyl alcohols and 3‐substituted 1H‐indoles. Not only is excellent chemoselectivity observed according to the substitution patterns of propargyl alcohols, but also the Lewis acid‐catalyzed NC bond formation process can be carried out under base‐ and ligand‐free conditions.