C-H Bond Cleavage by Bioinspired Nonheme Oxoiron(IV) Complexes, Including Hydroxylation of n-Butane.

作者: Scott T. Kleespies , Williamson N. Oloo , Anusree Mukherjee , Lawrence Que

DOI: 10.1021/IC502786Y

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摘要: The development of efficient and selective hydrocarbon oxidation processes with low environmental impact remains a major challenge the 21st century because strong apolar nature C–H bond. Naturally occurring iron-containing metalloenzymes can, however, selectively functionalize bonds on substrates under mild environmentally benign conditions. key oxidant in number these transformations is postulated to possess an S = 2 FeIV═O unit nonheme ligand environment. This has been trapped spectroscopically characterized its reactivity toward demonstrated for several iron enzyme classes. In order obtain insight into structure–activity relationships reactive intermediates, over 60 synthetic FeIV(O) complexes have prepared various laboratories their reactivities investigated. Forum Article summarizes current status efforts characterization bond cleavage syn...

参考文章(87)
Bernard Meunier, Gary Brudvig, Jennifer L Mclain, Shun-ichi Murahashi, VL Pecoraro, D Riley, Anne Robert, JA Rodriguez, RA Sheldon, JS Valentine, C Young, James M Mayer, Julian Limburg, Jinbo Lee, Diane Cabelli, RH Crabtree, Sergiu M Gorun, John T Groves, Zhengbo Hu, KU Ingold, Kenneth D Karlin, Naruyoshi Komiya, Marie-aude Kopf, Hans Jorg Krueger, H Zhu, Biomimetic oxidations catalyzed by transition metal complexes Imperial College Press. ,(2000) , 10.1142/P084
M. H. Lim, J.-U. Rohde, A. Stubna, M. R. Bukowski, M. Costas, R. Y. N. Ho, E. Munck, W. Nam, L. Que, An FeIV=O complex of a tetradentate tripodal nonheme ligand. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 100, pp. 3665- 3670 ,(2003) , 10.1073/PNAS.0636830100
Genqiang Xue, Alexander Pokutsa, Lawrence Que, Substrate-triggered activation of a synthetic [Fe2(μ-O)2] diamond core for C-H bond cleavage. Journal of the American Chemical Society. ,vol. 133, pp. 16657- 16667 ,(2011) , 10.1021/JA207131G
Jason England, Yisong Guo, Katherine M. Van Heuvelen, Matthew A. Cranswick, Gregory T. Rohde, Emile L. Bominaar, Eckard Münck, Lawrence Que, A more reactive trigonal-bipyramidal high-spin oxoiron(IV) complex with a cis-labile site Journal of the American Chemical Society. ,vol. 133, pp. 11880- 11883 ,(2011) , 10.1021/JA2040909
Andrei N. Vedernikov, Direct Functionalization of M–C (M = PtII, PdII) Bonds Using Environmentally Benign Oxidants, O2 and H2O2 Accounts of Chemical Research. ,vol. 45, pp. 803- 813 ,(2012) , 10.1021/AR200191K
Miquel Costas, Mark P. Mehn, Michael P. Jensen, Lawrence Que, Dioxygen Activation at Mononuclear Nonheme Iron Active Sites:  Enzymes, Models, and Intermediates Chemical Reviews. ,vol. 104, pp. 939- 986 ,(2004) , 10.1021/CR020628N
Danica P Galonić, Eric W Barr, Christopher T Walsh, J Martin Bollinger, Carsten Krebs, Two interconverting Fe( IV ) intermediates in aliphatic chlorination by the halogenase CytC3 Nature Chemical Biology. ,vol. 3, pp. 113- 116 ,(2007) , 10.1038/NCHEMBIO856
Aidan R. McDonald, Lawrence Que, High-valent nonheme iron-oxo complexes: Synthesis, structure, and spectroscopy Coordination Chemistry Reviews. ,vol. 257, pp. 414- 428 ,(2013) , 10.1016/J.CCR.2012.08.002