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Efficient and selective oxidation of primary and secondary alcohols using an iron(III)/phenanthroline complex: Structural studies and catalytic activity

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Biswas, B. [Sidho-Kanho-Birsha University (India)] Al-Hunaiti, A. [University of Helsinki (Finland)] Räisänen, M.T. [University of Helsinki (Finland)] Ansalone, S. [University of Helsinki (Finland)] Leskelä, M. [University of Helsinki (Finland)] Naik, Anil D. [UCL] Railliet, Antoine [UCL] Garcia, Yann [UCL] Kole, N. [Sidho-Kanho-Birsha University (India)]

An efficient catalytic system for the oxidation of alcohols has been developed by using iron(III) catalyst [Fe(phen) 2Cl 2]NO 3 (1) (phen = 1,10-phenanthroline) and H 2O 2 as terminal oxidant. A series of primary and secondary alcohols were oxidized into aldehydes and ketones in good yields and excellent selectivities after a short reaction time. The mononuclear iron(III) complex [Fe(phen) 2Cl 2]NO 3 was characterized by several independent methods. The X-ray structure shows distorted octahedral geometry around the Fe III center, which is in a high-spin state (S = 5/2) according to Mössbauer study. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2012
Language Anglais
Journal information "European Journal of Inorganic Chemistry" - Vol. --, no.28, p. 4479-4485 (2012)
Peer reviewed yes
Publisher Willey-VCH Verlag
issn 1434-1948
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords Alcohols ; Homogeneous catalysis ; Iron ; Ketones ; Oxidation
Links
  1. Cavani Fabrizio, Teles Joaquim Henrique, Sustainability in Catalytic Oxidation: An Alternative Approach or a Structural Evolution?, 10.1002/cssc.200900020
  2. Sheldon, Metal-Catalyzed Oxidation of Organic Compounds (1981)
  3. Iwahama T, Aerobic Oxidation of Alcohols to Carbonyl Compounds Catalyzed by N-Hydroxyphthalimide (NHPI) Combined with Co(acac)3, 10.1016/00404-0399(50)1431g-
  4. Sharma Vishal B, Jain Suman L, Sain Bir, Cobalt phthalocyanine catalyzed aerobic oxidation of secondary alcohols: an efficient and simple synthesis of ketones, 10.1016/s0040-4039(02)02453-x
  5. Minisci, J. Mol. Catal. A, 63, 204 (2003)
  6. Minisci Francesco, Punta Carlo, Recupero Francesco, Mechanisms of the aerobic oxidations catalyzed by N-hydroxyderivatives, 10.1016/j.molcata.2006.02.011
  7. Guo Hongfan, Al-Hunaiti Afnan, Kemell Marianna, Rautiainen Sari, Leskelä Markku, Repo Timo, Gold Catalysis Outside Nanoscale: Bulk Gold Catalyzes the Aerobic Oxidation of π-Activated Alcohols, 10.1002/cctc.201100286
  8. Guo Hongfan, Kemell Marianna, Al-Hunaiti Afnan, Rautiainen Sari, Leskelä Markku, Repo Timo, Gold–palladium supported on porous steel fiber matrix: Structured catalyst for benzyl alcohol oxidation and benzyl amine oxidation, 10.1016/j.catcom.2011.04.025
  9. Marko I. E., Giles P. R., Tsukazaki M., Brown S. M., Urch C. J., Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative, 10.1126/science.274.5295.2044
  10. Mound J. E., True Polar Wander as a Mechanism for Second-Order Sea-Level Variations, 10.1126/science.279.5350.534
  11. Chaudhuri Phalguni, Hess Martina, Flörke Ulrich, Wieghardt Karl, Vom Strukturmodell der Galactose-Oxidase zur homogenen Katalyse: effiziente aerobe Oxidation von Alkoholen, 10.1002/(sici)1521-3757(19980817)110:16<2340::aid-ange2340>3.0.co;2-c
  12. Markó István E., Gautier Arnaud, Chellé-Regnaut Isabelle, Giles Paul R., Tsukazaki Masao, Urch Christopher J., Brown Stephen M., Efficient and Practical Catalytic Oxidation of Alcohols Using Molecular Oxygen†, 10.1021/jo980770h
  13. Markó István. E., Giles Paul R., Tsukazaki Masao, Chellé-Regnaut Isabelle, Gautier Arnaud, Brown Stephen M., Urch Christopher J., Efficient, Ecologically Benign, Aerobic Oxidation of Alcohols†, 10.1021/jo982239s
  14. Chaudhuri Phalguni, Hess Martina, Müller Jochen, Hildenbrand Knut, Bill Eckhard, Weyhermüller Thomas, Wieghardt Karl, Aerobic Oxidation of Primary Alcohols (Including Methanol) by Copper(II)− and Zinc(II)−Phenoxyl Radical Catalysts, 10.1021/ja991481t
  15. Markó István E, Gautier Arnaud, Mutonkole Jean-Luc, Dumeunier Raphaël, Ates Ali, Urch Christopher J, Brown Stephen M, Neutral, non-racemising, catalytic aerobic oxidation of alcohols, 10.1016/s0022-328x(01)00681-7
  16. Ben-Daniel Revital, Alsters Paul, Neumann Ronny, Selective Aerobic Oxidation of Alcohols with a Combination of a Polyoxometalate and Nitroxyl Radical as Catalysts, 10.1021/jo0105843
  17. Matsumoto Masakatsu, Watanabe Nobuko, Oxidation of allylic alcohols to unsaturated carbonyl compounds by ruthenium dioxide and dioxygen/ruthenium dioxide, 10.1021/jo00192a054
  18. Yamaguchi Kazuya, Mori Kohsuke, Mizugaki Tomoo, Ebitani Kohki, Kaneda Kiyotomi, Creation of a Monomeric Ru Species on the Surface of Hydroxyapatite as an Efficient Heterogeneous Catalyst for Aerobic Alcohol Oxidation, 10.1021/ja001325i
  19. Shimizu Hideki, Onitsuka Satoaki, Egami Hiromichi, Katsuki Tsutomu, Ruthenium(salen)-Catalyzed Aerobic Oxidative Desymmetrization ofmeso-Diols and Its Kinetics, 10.1021/ja047608i
  20. Mori Shigeki, Takubo Masato, Makida Kazuya, Yanase Takayoshi, Aoyagi Satoka, Maegawa Tomohiro, Monguchi Yasunari, Sajiki Hironao, A simple and efficient oxidation of alcohols with ruthenium on carbon, 10.1039/b908451g
  21. Steinhoff Bradley A., Fix Shannon R., Stahl Shannon S., Mechanistic Study of Alcohol Oxidation by the Pd(OAc)2/O2/DMSO Catalyst System and Implications for the Development of Improved Aerobic Oxidation Catalysts, 10.1021/ja016806w
  22. Uozumi Yasuhiro, Nakao Ryu, 10.1002/ange.200390044
  23. Mueller Jaime A., Cowell Anne, Chandler Bert D., Sigman Matthew S., Origin of Enantioselection in Chiral Alcohol Oxidation Catalyzed by Pd[(−)-sparteine]Cl2, 10.1021/ja053195p
  24. Chen Tao, Jiang Jia-Jun, Xu Qin, Shi Min, Axially Chiral NHC−Pd(II) Complexes in the Oxidative Kinetic Resolution of Secondary Alcohols Using Molecular Oxygen as a Terminal Oxidant, 10.1021/ol063061w
  25. Shi Feng, Tse Man Kin, Pohl Marga-Matina, Radnik Jörg, Brückner Angelika, Zhang Shengmao, Beller Matthias, Nano-iron oxide-catalyzed selective oxidations of alcohols and olefins with hydrogen peroxide, 10.1016/j.molcata.2008.06.008
  26. Shi Feng, Tse Man Kin, Li Zuopeng, Beller Matthias, Controlling Iron-Catalyzed Oxidation Reactions: From Non-Selective Radical to Selective Non-Radical Reactions, 10.1002/chem.200801432
  27. Shi Feng, Tse Man Kin, Pohl Marga-Matina, Brückner Angelika, Zhang Shengmao, Beller Matthias, Tuning Catalytic Activity between Homogeneous and Heterogeneous Catalysis: Improved Activity and Selectivity of Free Nano-Fe2O3 in Selective Oxidations, 10.1002/ange.200703418
  28. Nakanishi Masafumi, Bolm Carsten, Iron-Catalyzed Benzylic Oxidation with Aqueoustert-Butyl Hydroperoxide, 10.1002/adsc.200600553
  29. Balogh-Hergovich Éva, Speier Gábor, Catalytic oxidation of alcohols to carbonyl compounds with hydrogen peroxide using dinuclear iron complexes, 10.1016/j.molcata.2004.12.013
  30. Tetrahedron Lett. 2003 44
  31. Yin Weili, Chu Changhu, Lu Qiongqiong, Tao Jianwei, Liang Xinmiao, Liu Renhua, Iron Chloride/4-Acetamido-TEMPO/Sodium Nitrite-Catalyzed Aerobic Oxidation of Primary Alcohols to the Aldehydes, 10.1002/adsc.200900662
  32. Pearson Anthony J., Kwak Yoonhyun, A new method for the selective oxidation of allylic and benzylic alcohols, 10.1016/j.tetlet.2005.05.147
  33. Ghosh Anindya, Tiago de Oliveira Filipe, Yano Toshihiro, Nishioka Takanori, Beach Evan S., Kinoshita Isamu, Münck Eckard, Ryabov Alexander D., Horwitz Colin P., Collins Terrence J., Catalytically Active μ-Oxodiiron(IV) Oxidants from Iron(III) and Dioxygen, 10.1021/ja0460458
  34. Wang Naiwei, Liu Renhua, Chen Jiping, Liang Xinmiao, NaNO2-activated, iron–TEMPO catalyst system for aerobic alcohol oxidation under mild conditions, 10.1039/b509167e
  35. Martı́n Sandra E, Suárez Darı́o F, Catalytic aerobic oxidation of alcohols by Fe(NO3)3–FeBr3, 10.1016/s0040-4039(02)00829-8
  36. Adolfsson, Modern Oxidation Methods (2011)
  37. Schröder Kristin, Join Benoît, Amali Arlin Jose, Junge Kathrin, Ribas Xavi, Costas Miquel, Beller Matthias, Ein biomimetischer Eisenkatalysator für die Epoxidation von Olefinen mit molekularem Sauerstoff bei Raumtemperatur, 10.1002/ange.201004623
  38. Schröder Kristin, Junge Kathrin, Spannenberg Anke, Beller Matthias, Design of a bio-inspired imidazole-based iron catalyst for epoxidation of olefins: Mechanistic insights, 10.1016/j.cattod.2010.04.034
  39. Rose Eric, Gallo Emma, Raoul Nicolas, Bouché Léa, Pille Ariane, Caselli Alessandro, Lequin Olivier, Chiral "basket handle" binaphthyl porphyrins: synthesis, catalytic epoxidation and NMR conformational studies, 10.1142/s1088424610002483
  40. Das Parthapratim, Que Lawrence, Iron Catalyzed Competitive Olefin Oxidation andipso-Hydroxylation of Benzoic Acids: Further Evidence for an FeV═O Oxidant, 10.1021/ic101144s
  41. Kinen Claudio O., Rossi Laura I., de Rossi Rita H., Mechanism of the Selective Sulfide Oxidation Promoted by HNO3/FeBr3, 10.1021/jo9015248
  42. Kinen Claudio Omar, Rossi Laura Isabel, de Rossi Rita Hoyos, The development of an environmentally benign sulfideoxidation procedure and its assessment by green chemistry metrics, 10.1039/b815986f
  43. Legros Julien, Bolm Carsten, Investigations on the Iron-Catalyzed Asymmetric Sulfide Oxidation, 10.1002/chem.200400857
  44. Legros Julien, Bolm Carsten, Highly Enantioselective Iron-Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions, 10.1002/ange.200460236
  45. Legros Julien, Bolm Carsten, Iron-Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide, 10.1002/ange.200352635
  46. Bigi Marinus A., Reed Sean A., White M. Christina, Diverting non-haem iron catalysed aliphatic C–H hydroxylations towards desaturations, 10.1038/nchem.967
  47. Oldenburg Paul D., Feng Yan, Pryjomska-Ray Iweta, Ness Daniel, Que Lawrence, OlefinCis-Dihydroxylation with Bio-Inspired Iron Catalysts. Evidence for an FeII/FeIVCatalytic Cycle, 10.1021/ja1021014
  48. Chen M. S., White M. C., Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation, 10.1126/science.1183602
  49. Feng Yan, Ke Chun-yen, Xue Genqiang, Que Lawrence, Bio-inspired arenecis-dihydroxylation by a non-haem iron catalyst modeling the action of naphthalene dioxygenase, 10.1039/b817222f
  50. Gómez Laura, Garcia-Bosch Isaac, Company Anna, Benet-Buchholz Jordi, Polo Alfonso, Sala Xavier, Ribas Xavi, Costas Miquel, Stereospecific CH Oxidation with H2O2Catalyzed by a Chemically Robust Site-Isolated Iron Catalyst, 10.1002/ange.200901865
  51. Molinari Raffaele, Poerio Teresa, Selectivity control of benzene conversion to phenol using dissolved salts in a membrane contactor, 10.1016/j.apcata.2010.12.018
  52. Mi Guanjie, Li Jianwei, Zhang Jie, Chen Biaohua, Reaction kinetics of phenol synthesis through one-step oxidation of benzene with N2O over Fe-ZSM-5 zeolite, 10.1007/s11814-010-0259-7
  53. Rana Bharat S., Singh Bhawan, Kumar Rohit, Verma Deepak, Bhunia Manas K., Bhaumik Asim, Sinha Anil K., Hierarchical mesoporous Fe/ZSM-5 with tunable porosity for selective hydroxylation of benzene to phenol, 10.1039/c0jm01586e
  54. Makhlynets Olga V., Das Parthapratim, Taktak Sonia, Flook Margaret, Mas-Ballesté Rubén, Rybak-Akimova Elena V., Que Lawrence, Iron-Promotedortho- and/oripso-Hydroxylation of Benzoic Acids with H2O2, 10.1002/chem.200901296
  55. Chen Xiufang, Zhang Jinshui, Fu Xianzhi, Antonietti Markus, Wang Xinchen, Fe-g-C3N4-Catalyzed Oxidation of Benzene to Phenol Using Hydrogen Peroxide and Visible Light, 10.1021/ja903923s
  56. Chem. News, 33, 190 (1876)
  57. Proc. Chem. Soc., 10, 157 (1894)
  58. Walling Cheves, Intermediates in the Reactions of Fenton Type Reagents, 10.1021/ar9700567
  59. Barton Derek H. R., Doller Dario, The selective functionalization of saturated hydrocarbons: Gif chemistry, 10.1021/ar00023a004
  60. Perkins M. John, A radical reappraisal of Gif reactions, 10.1039/cs9962500229
  61. Barton Derek H. R., Hu Bin, Taylor Dennis K., Wahl Roy U. Rojas, The selective functionalization of saturated hydrocarbons. Part 32. Distinction between the FeII–FeIVand FeIII–FeVmanifolds in Gif chemistry. The importance of carboxylic acids for alkane activation. Evidence for a dimeric iron species involved in Gif-type chemistry, 10.1039/p29960001031
  62. Al-Hunaiti Afnan, Niemi Teemu, Sibaouih Ahlam, Pihko Petri, Leskelä Markku, Repo Timo, Solvent free oxidation of primary alcohols and diols using thymine iron(iii) catalyst, 10.1039/c0cc04043f
  63. Yin, Adv. Synth. Catal., 352, 113 (2010)
  64. Chelucci Giorgio, Thummel Randolph P., Chiral 2,2‘-Bipyridines, 1,10-Phenanthrolines, and 2,2‘:6‘,2‘ ‘-Terpyridines:  Syntheses and Applications in Asymmetric Homogeneous Catalysis, 10.1021/cr0101914
  65. Menage Stephane, Vincent Jean Marc, Lambeaux Claude, Chottard Genevieve, Grand Andre, Fontecave Marc, Alkane oxidation catalyzed by .mu.-oxo-bridged diferric complexes: a structure/reactivity correlation study, 10.1021/ic00074a019
  66. Ménage Stéphane, Vincent Jean-Marc, Lambeaux Claude, Fontecave Marc, Alkane oxidation catalyzed by μ-oxo bridged diferric complexes: an overall mechanism, 10.1016/s1381-1169(96)00090-8
  67. Gritsenko O. N., Nesterenko G. N., Shteinman A. A., Effect of substituents in the ligand on oxidation of alkanes catalyzed by binuclear oxo-bridged iron complexes, 10.1007/bf00713616
  68. Kulikova Vera S., Gritsenko Olga N., Shteinman Albert A., Molecular mechanism of alkane oxidation involving binuclear iron complexes, 10.1070/mc1996v006n03abeh000608
  69. Goodwin H.J., McPartlin M., Goodwin H.A., structure of dichlorobis(1,10-phenanthroline)iron (III) tetrachloroferrate(III), 10.1016/s0020-1693(00)95651-2
  70. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds (1997)
  71. Bishop D. F., Stern G., Fleischman M., Marshall L. S., Hydrogen Peroxide Catalytic Oxidation of Refractory Organics in Municipal Waste Waters, 10.1021/i260025a022
  72. Eisenhauer, J. Water Pollut. Control Fed., 36, 1116 (1964)
  73. Feuerstein, Vom Wasser, 56, 34 (1981)
  74. Base, The Hydrolysis of Cations (1976)
  75. Pourbaix, Atlas d'Équilibres Électrochimiques (1963)
  76. Barton Derek H.R., Bévière Stéphane D., Chabot Béatrice M., Chavasiri Warinthorn, Taylor Dennis K., Studies on the oxidation of alcohols employing t-butyl hydroperoxide (TBHP) and Fe(III) catalysts, 10.1016/s0040-4039(00)76940-1
  77. Collins R.L., Pettit R., Baker W.A., Mössbauer studies of iron organometallic complexes—III, 10.1016/0022-1902(66)80196-3
  78. Ginsberg A. P., Robin M. B., The Structure, Spectra, and Magnetic Properties of Certain Iron Halide Complexes, 10.1021/ic50008a038
  79. Hall Lou Henry., Spijkerman Jon J., Lambert Jack L., Preparation and coordination studies of the complex acid, dihydrogen diethylenetriaminepentaacetatoferrate(III) dihydrate, and several of its metal(I) salts, 10.1021/ja01010a024
  80. Recoil 1998
  81. SHELXTL 1997
Bibliographic reference Biswas, B. ; Al-Hunaiti, A. ; Räisänen, M.T. ; Ansalone, S. ; Leskelä, M. ; et. al. Efficient and selective oxidation of primary and secondary alcohols using an iron(III)/phenanthroline complex: Structural studies and catalytic activity . In: European Journal of Inorganic Chemistry, Vol. --, no.28, p. 4479-4485 (2012)
Permanent URL http://hdl.handle.net/2078.1/125588