A diiron(II) complex containing two mu-1,3(kappa N:kappa O)-amidate linkages has been synthesized using the 2,2',2 ''-tris(isobutyrylamido)triphenylamine (H3LiPr) ligand. The resulting diiron complex, 1, reacts with dioxygen (or iodosylbenzene) to effect intramolecular C-H bond activation at the methine position of the ligand isopropyl group. The ligand-activated product, 2, has been isolated and characterized by a variety of methods including X-ray crystallography. Electrospray ionization mass spectroscopy of 2 prepared from (18)(2) was used to confirm that the oxygen atom incorporated into the ligand framework is derived from molecular oxygen.