Rh(III)-catalyzed successive C-H activations of 2-phenyl-3H-indoles and cyclization cascades with diazo compounds were developed to construct highly fused indole heteropolycycles with a broad range of substrates and good yields. In particular, this transformation included two successive C-H activations and unusual [3+3] and [4+2] sequential cyclization cascades, in which the diazo compound played a different role in the two cyclization processes, while simultaneously forming a highly fused polycyclic indole scaffold with a new quaternary carbon center.