An Fe(OTf)3-catalyzed 1,5-enyne cycloisomerization via 5-endo-dig cyclization is described for the synthesis of 3-(1-indenyl)indole derivatives. Since a variety of 1,5-enynes are readily accessible via Heck-Suzuki coupling, this strategy provides a rapid and easy access to a wide range of highly substituted 3-(1-indenyl)indoles in good yields.