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Pure Appl. Chem., 1987, Vol. 59, No. 6, pp. 759-770

http://dx.doi.org/10.1351/pac198759060759

Cytochrome P-450 and synthetic models

D. Mansuy

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  • Fackler Philipp, Huber Stefan M., Bach Thorsten: Enantio- and Regioselective Epoxidation of Olefinic Double Bonds in Quinolones, Pyridones, and Amides Catalyzed by a Ruthenium Porphyrin Catalyst with a Hydrogen Bonding Site. J. Am. Chem. Soc. 2012, 134, 12869. <http://dx.doi.org/10.1021/ja305890c>
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  • Kargar Hadi, Afkhami Saeideh, Alikhani Fatemeh: Green oxidation of 2-imidazolines with tert-butyl hydroperoxide catalyzed by supported manganese(III) porphyrin in water. Journal of Coordination Chemistry 2012, 65, 3502. <http://dx.doi.org/10.1080/00958972.2012.720016>
  • Solati Zahra, Hashemi Majid, Ebrahimi Leila: Rapid and Highly Selective Epoxidation of Styrene by meta-Chloroperbenzoic Acid Catalyzed by Manganese Meso-tetrakis(Pentafluorophenyl)Porphyrin in the Presence of Tetrabutylammonium Acetate and Bromide. Catal Lett 2011, 141, 163. <http://dx.doi.org/10.1007/s10562-010-0460-7>
  • Kargar Hadi, Moghadam Majid, Mirkhani Valiollah, Tangestaninejad Shahram, Mohammadpoor-Baltork Iraj, Nameni Iman: Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin. Biorg Med Chem Lett 2011, 21, 2146. <http://dx.doi.org/10.1016/j.bmcl.2011.01.126>
  • Kargar Hadi, Moghadam Majid, Mirkhani Valiollah, Tangestaninejad Shahram, Mohammadpoor-Baltork Iraj, Naghipour Mahmood: Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin. J Polyhedron 2011, 30, 1463. <http://dx.doi.org/10.1016/j.poly.2011.02.040>
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  • Dong-Hong Li, Shu-Hua Chen, Hua-Ming Zhao: Calix[6]arene-bismetalloporphyrins as Enzyme Models for P450 V. Catalytic Performance in Epoxidation of Styrene. Chin J Chem 2010, 21, 683. <http://dx.doi.org/10.1002/cjoc.20030210621>
  • Banfi S., Montanari F., Quici S.: Steric and electron-withdrawing effects of substituents governing chemical stability and catalytic activity of Mn(III)-tetraarylporphyrins in HOCl/ClO− alkene expoxidations. Recl Trav Chim Pays-Bas 2010, 109, 117. <http://dx.doi.org/10.1002/recl.19901090217>
  • Hansen Carola B., Mul Guido, Tabor Roland B. J., Drenth Wiendelt: Mechanistic study of decomposition of cyclohexyl hydroperoxide catalysed by manganese(III) tetraarylporphyrins. Recl Trav Chim Pays-Bas 2010, 112, 497. <http://dx.doi.org/10.1002/recl.19931120903>
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  • Ye Yuan-Jian, Huang Jin-Wang, Cai Jin-Hua, Yu Han-Cheng, Wu Wen-Hai, Zhou Xian-Tai, Ji Hong-Bin, Ji Liang-Nian: Styrene-hydroxyethyl methacrylate copolymer-supported porphyrinatomanganese(III) complexes: synthesis and catalytic cyclohexane hydroxylation with molecular oxygen. Trans Met Chem 2010, 35, 627. <http://dx.doi.org/10.1007/s11243-010-9373-y>
  • Fackler Philipp, Berthold Carola, Voss Felix, Bach Thorsten: Hydrogen-Bond-Mediated Enantio- and Regioselectivity in a Ru-Catalyzed Epoxidation Reaction. J Am Chem Soc 2010, 132, 15911. <http://dx.doi.org/10.1021/ja107601k>
  • Aghabali Amineh, Safari Nasser: Effects of methoxy-substituted metalloporphyrins in catalytic alkene epoxidation by n-Bu4NHSO5. J. Porphyrins Phthalocyanines 2010, 14, 335. <http://dx.doi.org/10.1142/S1088424610002136>
  • Mirkhani Valiollah, Moghadam Majid, Tangestaninejad Shahram, Mohammdpoor-Baltork Iraj, Kargar Hadi, Araghi Mehdi: Highly efficient oxidation of sulfides with sodium periodate catalyzed by reusable silica supported Mn(Br8TPP)Cl and Mn(TPP)Cl catalysts under various reaction conditions. CATAL A GENERAL 2009, 353, 61. <http://dx.doi.org/10.1016/j.apcata.2008.10.021>
  • Fu Bo, Yu Han-Cheng, Huang Jin-Wang, Zhao Ping, Liu Jie, Ji Liang-Nian: Mn(III) porphyrins immobilized on magnetic polymer nanospheres as biomimetic catalysts hydroxylating cyclohexane with molecular oxygen. Journal of Molecular Catalysis A 2009, 298, 74. <http://dx.doi.org/10.1016/j.molcata.2008.10.015>
  • Moghadam Majid, Mohammadpoor-Baltork Iraj, Tangestaninejad Shahram, Mirkhani Valiollah, Kargar Hadi, Zeini-Isfahani Nafiseh: Manganese(III) porphyrin supported on multi-wall carbon nanotubes: A highly efficient and reusable biomimetic catalyst for epoxidation of alkenes with sodium periodate. J Polyhedron 2009, 28, 3816. <http://dx.doi.org/10.1016/j.poly.2009.08.016>
  • Che Chi-Ming, Huang Jie-Sheng: Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis. Chem Commun 2009, 3996. <http://dx.doi.org/10.1039/b901221d>
  • Doǧan F., Ulusoy M., Öztürk Ö. F., Kaya İ., Salih B.: N,N′-bis(3,5-di-t-butylsalicylideneimine)propanediamine and its some tetradentate Schiff base complexes. J Therm Anal Calorim 2008. <http://dx.doi.org/10.1007/s10973-008-9099-7>
  • Wei Xing-Yue, Qin Sheng-Ying: Dioxygen affinities and catalytic oxidation performance of cobalt(II) dihydroxamic acids with central functional group. React Kinet Catal Lett 2008, 95, 337. <http://dx.doi.org/10.1007/s11144-008-5401-8>
  • Moghadam Majid, Mirkhani Valiollah, Tangestaninejad Shahram, Mohammdpoor-Baltork Iraj, Kargar Hadi: Silica supported Mn(Br8TPP)Cl and Mn(TPP)Cl as efficient and reusable catalysts for selective hydrocarbon oxidation under various reaction conditions: The effect of substituted bromines on the catalytic activity and reusability. Journal of Molecular Catalysis A 2008, 288, 116. <http://dx.doi.org/10.1016/j.molcata.2008.03.028>
  • Rayati Saeed, Zakavi Saeed, Motlagh Somayeh H., Noroozi Vahid, Razmjoo Maryam, Wojtczak Andrzej, Kozakiewicz Anna: β-Tetra-brominated meso-tetraphenylporphyrin: A conformational study and application to the Mn-porphyrin catalyzed epoxidation of olefins with tetrabutylammonium oxone. J Polyhedron 2008, 27, 2285. <http://dx.doi.org/10.1016/j.poly.2008.04.019>
  • Chouthaiwale Pandurang V., Suryavanshi Gurunath, Sudalai Arumugam: NaIO4–KI–NaN3 as a new reagent system for C–H functionalization in hydrocarbons. Tetrahetron Lett 2008, 49, 6401. <http://dx.doi.org/10.1016/j.tetlet.2008.08.071>
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  • Pouralimardan Omid, Chamayou Anne-Christine, Janiak Christoph, Hosseini-Monfared Hassan: Hydrazone Schiff base-manganese(II) complexes: Synthesis, crystal structure and catalytic reactivity. Inorg Chim Ada 2007, 360, 1599. <http://dx.doi.org/10.1016/j.ica.2006.08.056>
  • Hassanein M., Gerges S., Abdo M., EL-Khalafy S.: Autoxidation of 2,6-di-tert-butylphenol catalyzed by 5,10,15,20-tetrakis[4-(diethylmethylammonio)phenyl]porphyrinatocobalt(II) tetraiodide in water. Journal of Molecular Catalysis A 2007, 268, 24. <http://dx.doi.org/10.1016/j.molcata.2006.11.045>
  • Stephenson Ned A., Bell Alexis T.: Effects of porphyrin composition on the activity and selectivity of the iron(III) porphyrin catalysts for the epoxidation of cyclooctene by hydrogen peroxide. Journal of Molecular Catalysis A 2007, 272, 108. <http://dx.doi.org/10.1016/j.molcata.2007.03.030>
  • Stephenson Ned A., Bell Alexis T.: Mechanistic insights into iron porphyrin-catalyzed olefin epoxidation by hydrogen peroxide: Factors controlling activity and selectivity. Journal of Molecular Catalysis A 2007, 275, 54. <http://dx.doi.org/10.1016/j.molcata.2007.05.005>
  • Nakayama Nirei, Tsuchiya Shinji, Ogawa Shojiro: Hydrocarbon oxidation with hydrogen peroxide and pentafluoroiodosylbenzene catalyzed by unusually distorted macrocycle manganese complexes. Journal of Molecular Catalysis A 2007, 277, 61. <http://dx.doi.org/10.1016/j.molcata.2007.07.017>
  • Lübbe Andrea Nicola, Rickerts Bianca, Duchstein Hans-Jürgen: Comparison of Activity of Immobilised and Soluble Metalloporphyrins by NO Release of Oximes by Chemiluminescence. Arch Pharm Pharm Med Chem 2006, 339, 652. <http://dx.doi.org/10.1002/ardp.200600064>
  • Cabrera-Vivas B. M., Pineda Flor P., García-Hidalgo S., Múñoz-Arenas M. G., Meléndez F. J., Reyes-Ortega Y., Ramírez Juan Carlos: Theoretical study of structural features of endo, exo double bonds and side chain in 14α-demethylation of lanosterol. Int J Quantum Chem 2006, 106, 542. <http://dx.doi.org/10.1002/qua.20778>
  • Mirkhani Valiollah, Moghadam Majid, Tangestaninejad Shahram, Kargar Hadi: Mn(Br8TPP)Cl supported on polystyrene-bound imidazole: An efficient and reusable catalyst for biomimetic alkene epoxidation and alkane hydroxylation with sodium periodate under various reaction conditions. CATAL A GENERAL 2006, 303, 221. <http://dx.doi.org/10.1016/j.apcata.2006.02.007>
  • Nasr-Esfahani Masoud, Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Momeni Ahmad Reza: Rapid and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by manganese (III) Schiff base complexes. biorg med chem 2006, 14, 2720. <http://dx.doi.org/10.1016/j.bmc.2005.11.051>
  • Lai Tat-Shing, Chan Fung-Yi, So Pui-Kin, Ma Dik-Lung, Wong Kwok-Yin, Che Chi-Ming: Alkene cyclopropanation catalyzed by Halterman iron porphyrin: participation of organic bases as axial ligands. Dalton Trans 2006, 4845. <http://dx.doi.org/10.1039/b606757c>
  • Nasr-Esfahani Masoud, Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah: Biomimetic oxidation of Hantzsch 1,4-dihydropyridines with tetra-n-butylammonium periodate catalyzed by tetraphenylporphyrinatomanganese(III) chloride [Mn(TPP)Cl]. Biorg Med Chem Lett 2005, 15, 3276. <http://dx.doi.org/10.1016/j.bmcl.2005.04.044>
  • Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Kargar Hadi, Komeili-Isfahani Hedyeh: Polystyrene-bound imidazole as a heterogeneous axial ligand for Mn(TPP)Cl and its use as hydrocarbon monooxygenation catalyst in the alkene epoxidation and alkane hydroxylation with sodium periodate under various reaction conditions. Catal Commun 2005, 6, 688. <http://dx.doi.org/10.1016/j.catcom.2005.06.012>
  • Mirkhani Valiollah, Tangestaninejad Shahram, Moghadam Majid, Mohammadpoor-Baltork Iraj, Kargar Hadi: Efficient oxidation of sulfides with sodium periodate catalyzed by manganese(III) Schiff base complexes. Journal of Molecular Catalysis A 2005, 242, 251. <http://dx.doi.org/10.1016/j.molcata.2005.07.045>
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  • Moghadam Majid, Moghbel Maryam, Mirkhani Valiollah, Tangestaninejad Shahram: Rapid and efficient oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by manganese (III) Schiff base complexes. biorg med chem 2004, 12, 903. <http://dx.doi.org/10.1016/j.bmc.2003.12.025>
  • Mirkhani Valiollah, Tangestaninejad Shahram, Moghadam Majid, Karimian Zohreh: Efficient oxidative decarboxylation of carboxylic acids with sodium periodate catalyzed by supported manganese (III) porphyrin. Biorg Med Chem Lett 2003, 13, 3433. <http://dx.doi.org/10.1016/S0960-894X(03)00749-2>
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