Direct C-H bond arylation of a wide range of functionalized (NH)-free indoles and pyrroles with aryl iodides was achieved in the presence of [Rh(coe)₂Cl₂]₂, [4-(CF₃)C₆H₄]₃P (both commercially available from Strem), and CsOPiv (readily synthesized from Cs₂CO₃). This procedure led to the isolation of 2-arylated indoles or pyrroles in good yields with excellent regioselectivities (>50:1). The reaction protocol also displayed excellent functional group compatibility and low moisture sensitivity, allowing convenient preparation of gram quantities of 2-phenyl indole in a single step without the use of column chromatograph or a glovebox. The catalyst resting state, a novel Ar-Rh(III) pivalate complex (1), was isolated and characterized via X-ray crystallography.  Kinetics studies support a mechanism involving phosphine displacement by indole in complex 1 (catalyst resting state) followed by a rate-limiting C-H bond metalation.