Photo-promoted cyanomethyl radical procedures for the efficient and simple preparation of 2,3-dihydro-1H-indenes and 2,8-dihydrocyclopenta[a]indenes from phenyl-linked 1,6-enynes with α-halogenated acetonitriles are reported. The iodocyanomethyla-tion/cyclization is performed via an atom-transfer radical addition (ATRA) strategy under photocatalyst- and oxidant-free conditions. In particular, the photoinduced cyanomethylative cascade bicyclization is carried out under the fac-Ir(ppy)3/Na2CO3 catalystic symtem and visible light irradiation. These methods offer a one-step and atom-economical access to diverse cyano-group containing five-membered rings with broad substrate scope and high selectivity. A plausible reaction mechanism is also proposed.