Nonheme diiron oxidation catalysts

INOR 757

Min Zhao, mzhao@mit.edu1, Brett A. Helms, bhelms@uclink.berkeley.edu2, Jean M. J. Frechét, Frechet@CChem.Berkeley.EDU2, and Stephen J. Lippard1. (1) Department of Chemistry, Massachusetts Institute of Technology, Building 18 Room 463, 77 Massachusetts Institute of Technology, Cambridge, MA 02139, (2) Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720-1460
The active sites of metalloenzymes are often deeply buried inside a hydrophobic protein sheath, which protects them from undesirable hydrolysis and polymerization reactions, allowing them to achieve their normal functions. In order to mimic the hydrophobic environment of the active sites in bacterial monooxygenases, diiron(II) compounds of the general formula [Fe2([G-3]COO)4(R)2] were prepared, where [G-3]COO- is a third-generation dendrimer-appended terphenyl carboxylate ligand and R is a pyridine derivative. The dendrimer environment provides excellent protection for the diiron center, reducing its reactivity toward dioxygen by about 300-fold compared with analogous compound with terphenylcarboxylate ([G-1]COO-) ligands. An Fe(II)Fe(III) intermediate was characterized by electronic, EPR, and Mössbauer spectroscopic analysis following oxygenation of [Fe2([G-3]COO)4(4-PPy)2] (4-PPy = 4-pyrrolidinopyridine). The results suggested formation of a superoxo species. This intermediate can oxidize external substrates. Catalytic reactivity was observed with anthrone as the substrate. A catalytic oxidation mechanism describing this chemistry has been formulated and will be discussed. This work was supported by the National Institute of General Medical Sciences (to SJL) and the National Science Foundation (DMR to JMJF).