Modeling TauD‑J: A High-Spin Nonheme Oxoiron(IV) Complex with High Reactivity toward C–H Bonds

High-spin oxoiron­(IV) species are often implicated in the mechanisms of nonheme iron oxygenases, their C–H bond cleaving properties being attributed to the quintet spin state. However, the few available synthetic S = 2 FeIVO complexes supported by polydentate ligands do not cleave strong C–H bonds. Herein we report the characterization of a highly reactive S = 2 complex, [FeIV(O)­(TQA)­(NCMe)]2+ (2) (TQA = tris­(2-quinolylmethyl)­amine), which oxidizes both C–H and CC bonds at −40 °C. The oxidation of cyclohexane by 2 occurs at a rate comparable to that of the oxidation of taurine by the TauD-J enzyme intermediate after adjustment for the different temperatures of measurement. Moreover, compared with other S = 2 complexes characterized to date, the spectroscopic properties of 2 most closely resemble those of TauD-J. Together these features make 2 the best electronic and functional model for TauD-J to date.