Herein we report the intramolecular arene C-H and C-F bond oxygenation by tetranuclear iron complexes. Treatment of [LFe3(PhPz)(3)OFe][OTf](2) (1) or its fluorinated analog [LFe3(F(2)ArPz)(3)OFe][OTf](2) (5) with iodosobenzene results in the regioselective hydroxylation of a bridging pyrazolate ligand, converting a C-H or C-F bond into a C-O bond. The observed reactivity suggests the formation of terminal and reactive Fe-oxo intermediates. With the possibility of intramolecular electron transfer within clusters in 1 and 5, different reaction pathways (Fe-IV-oxo vs Fe-III-oxo) might be responsible for the observed arene hydroxylation.