The Rh(III)-catalyzed C-H functionalization of sulfoxonium ylides and successively annulation with two classes of cyclic diazo compounds has been realized, affording structurally diverse fused-ring or spirocyclic compounds under redoxneutral conditions. The reaction proceeds via successive chelation-assisted C-H activation, carbene insertion, and intramolecular [3 + 3]/[4 + 1] annulation processes.