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Nonheme FeIVO Complexes That Can Oxidize the C−H Bonds of Cyclohexane at Room Temperature
Abstract
Nonheme oxoiron(IV) complexes of two pentadentate ligands, N4Py (N,N-bis(2-pyridylmethyl)-bis(2-pyridyl)methylamine) and Bn-tpen (N-benzyl-N,N',N'-tris(2-pyridylmethyl)-1,2-diaminoethane), have been generated and found to have spectroscopic properties similar to the closely related tetradentate TPA (tris(2-pyridylmethyl)amine) complex reported earlier. However, unlike the TPA complex, the pentadentate complexes have a considerable lifetime at room temperature. This greater thermal stability has allowed the hydroxylation of alkanes with C-H bonds as strong as 99.3 kcal/mol to be observed at room temperature. Furthermore, a large deuterium KIE value is found in the oxidation of ethylbenzene. These observations lend strong credence to postulated mechanisms of mononuclear nonheme iron enzymes that invoke the intermediacy of oxoiron(IV) species.
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Citations
Cited by
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Huynh, M. H. V., & Meyer, T. J. (2007) · Chemical Reviews · doi:10.1021/cr0500030 · Cited by 1,659
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Shaik, S., Cohen, S., Wang, Y., Chen, H., Kumar, D., & Thiel, W. (2010) · Chemical Reviews · doi:10.1021/cr900121s · Cited by 1,083
Reactivity of High-Valent Iron–Oxo Species in Enzymes and Synthetic Reagents: A Tale of Many States
Shaik, S., Hirao, H., & Kumar, D. (2007) · Accounts of Chemical Research · doi:10.1021/ar600042c · Cited by 555
Reactivity of Aqueous Fe(IV) in Hydride and Hydrogen Atom Transfer Reactions
Pestovsky, O., & Bakac, A. (2004) · Journal of the American Chemical Society · doi:10.1021/ja0457112 · Cited by 313
Nandy, A., Zhu, J., Janet, J. P., Duan, C., Getman, R. B., & Kulik, H. J. (2019) · ACS Catalysis · doi:10.1021/acscatal.9b02165 · Cited by 91
Metadata
- Authors
- Kaizer, J., Klinker, E. J., Oh, N. Y., Rohde, J.-U., Song, W. J., Stubna, A., Kim, J., Münck, E., Nam, W., & Que, L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-12-23
- Volume
- 126
- Issue
- 2
- Pages
- 472-473
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2057331738
- Cited by
- 647
- References
- 0
- FWCI
- 21.17
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kaizer, J., Klinker, E. J., Oh, N. Y., Rohde, J.-U., Song, W. J., Stubna, A., Kim, J., Münck, E., Nam, W., & Que, L. (2004). Nonheme FeIVO Complexes That Can Oxidize the C−H Bonds of Cyclohexane at Room Temperature. Journal of the American Chemical Society. https://doi.org/10.1021/ja037288n
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