An efficient approach for the preparation of tetracyclic indeno[1,2-b]indoles via Rh(III)-catalyzed C−H cascade annulation between ar-ylhydrazines and diazo indan-1,3-diones has been established. In addition, a series of indeno[1,2-b]indoles were obtained in up to 96% yield with a wide range of substrates and high functional group tolerance. Finally, the diverse transformations of the desired products demonstrate the synthetic utility and utilization of this protocol.