Lewis Acid Catalyzed Epoxidation of Olefins Using Hydrogen Peroxide: Growing Prominence and Expanding Range

Mechanisms in Homogeneous and Heterogeneous Epoxidation Catalysis

Volumn , Issue , 2008, Pages 119-153

  Busch, Daryle H ^a   Yin, Guochuan ^a   Lee, Hyun Jin ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84887566711     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-444-53188-9.00003-1     Document Type: Chapter

References (102)

1. Groves J.T. Key elements of the chemistry of cytochrome P-450. The oxygen rebound mechanism. J. Chem. Edu. 1985, 65:928.
2. Sharpless K.B. Searching for new reactivity (Nobel Lecture). Angew. Chem. Int. Ed. 2002, 41:2024.
3. Knowles W.S. Asymmetric hydrogenations (Nobel Lecture). Angew. Chem. Int. Ed. 2002, 41:1998.
4. Noyori R. Asymmetric catalysis: Science and opportunities (Nobel Lecture). Angew. Chem. Int. Ed. 2002, 41:2008.
5. Ortiz de Montellano P.R. Cytochrome P-450: Structure, Mechanism, and Biochemistry 1986, Plenum Press, New York, NY.
6. Porter T.D., Coon M.J. Cytochrome P-450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem. 1991, 266:13469.
7. Chance B. Enzyme-substrate compounds of horseradish peroxidase and peroxides. II. Kinetics of formation and decomposition of the primary and secondary complexes. Arch. Biochem. Biophys. 1949, 22:224.
8. McGarrigle E.M., Gilheany D.G. Chromium- and Manganese-salen Promoted Epoxidation of Alkenes. Chem. Rev. 2005, 105:1564.
9. Molnar A., Olah G.A. Oxidation of Alkenes, in: Hydrocarbon Chemistry 2003, 452-461. Wiley-Interscience, Hoboken, NJ.
10. Conte V., Di Furia F. Catalytic oxidations with hydrogen peroxide as oxidant. Peroxometal complexes derived from hydrogen peroxide. Some applications in organic synthesis. Catalysis by Metal Complexes 1992, 9:223-252.
11. Henbest H.B., Wilson R.A.I. Aspects of stereochemistry. I. Stereospecificity in formation of epoxides from cyclic allylic alcohols. J. Chem. Soc. 1957, 1958.
12. Sharpless K.B., Michaelson R.C. High stereo- and regioselectivities in the transition metal catalyzed epoxidations of olefinic alcohols by tert-butyl hydroperoxide. J. Am. Chem. Soc. 1973, 95:6136.
13. Woodard S.S., Finn M.G., Sharpless K.B. Mechanism of asymmetric epoxidation. I. Kinetics. J. Am. Chem. Soc. 1991, 113:106.
14. Finn M.G., Sharpless K.B. Mechanism of asymmetric epoxidation. I. Kinetics. J. Am. Chem. Soc. 1991, 113:113.
15. Trent D. Propylene Oxide. Encyclopedia of Chemical Technology 1996, Vol. 30:271-302. John Wiley & Sons, New York, NY. 4th ed.
16. Ullmann's Encyclopedia of Industrial Chemistry 1987, Vol. A9:531-564. Verlag Chemie, Weinheim. 5th ed.
17. Herrmann W.A., Dieter M., Wagner W., Kuchler J.G., Weichselbaumer G., Fischer R. Use of organorhenium compounds for the oxidation of multiple C-C bonds, oxidation based thereon and novel organorhenium compounds 1992, Assigned to Hoechst Aktiegesellschaft, U.S. Patent 5155247, Oct. 13.
18. G. L. Crocco, W. F. Shum, J. G. Zajacek, S. Kesling Jr., Epoxidation process, U.S. Patent, 5166372, Assigned to Arco Chemical Technology.
19. Venturello C., D'Alolslo R. Quaternary ammonium tetrakis(diperoxotungsto)phosphates(3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide. J. Org. Chem. 1988, 53:1553.
20. Venturello C., Alneri E., Ricci M. A new, effective catalytic system for epoxidation of olefins by hydrogen peroxide under phase-transfer conditions. J. Org. Chem. 1983, 48:3831.
21. Venturello C., D'Aloislo R., Bart J.C.J., Ricci M. A new peroxotungsten heteropoly anion with special oxidizing properties: Synthesis and structure of tetrahexylammonium tetra(diperoxotungsto)phosphate(3-). J. Mol. Catal. 1985, 32:107.
22. Sato K., Aki M., Ogawa M., Hashimoto T., Noyori R. A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J. Org. Chem. 1996, 61:8310.
23. Noyori R., Aoki M., Sato K. Green oxidation with aqueous hydrogen peroxide. Chem. Comm. 2003, 1977.
24. Maheswari P.U., de Hoog P., Hage R., Gamez P., Reedijk J. A Na2WO4/H2WO4-based highly efficient biphasic catalyst towards alkene epoxidation, using dihydrogen peroxide as oxidant. Adv. Synth. Catal. 2005, 347:1759.
25. Xi Z., Zou N., Sun Y., Li K. Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide. Science 2001, 292:1139.
26. Okuhara T., Mizuno N., Misono M. Catalytic chemistry of heteropoly compounds. Adv. Catal. 1996, 41:113.
27. Mizumo N., Nozaki C., Kiyoto I., Misono M. Highly efficient utilization of hydrogen peroxide for selective oxygenation of alkanes catalyzed by Diiron-substituted polyoxometalate precursor. J. Am. Chem. Soc. 1998, 120:9267.
28. Neumann R. Polyoxometalate complexes in organic oxidation chemistry. Prog. Inorg. Chem. 1998, 47:317.
29. Neumann R., Gara M. The Manganese-containing polyoxometalate, [WZnMnII2(ZnW9O34)2]12-, as a remarkably effective catalyst for hydrogen peroxide mediated oxidations. J. Am. Chem. Soc. 1995, 117:5066.
30. Cotton F.A., Wilkinson G. Advanced Inorganic Chemistry 1988, 816. John Wiley, New York, NY. 5th ed.
31. 399% selectivity and use of hydrogen mediated peroxide. Science 2003, 300:964.
32. Tullo H., Short P.L. Prepylene oxide routes take off. Chem. Eng. News 2006, 84(41):22.
33. Anastas P.T., Warner J.C. Green Chemistry. Theory and Practice 1998, Oxford University Press, Oxford, UK.
34. Lancaster M. Green Chemistry: An Introductory Text 2002, Royal Society of Chemistry, Cambridge, UK.
35. B. Subramaniam, D. H. Busch, H.-J. Lee, T.-P. Shi, Process for the selective oxidation of propylene to propylene oxide and facile separation of propylene oxide, U.S. Provisional Patent filled 10/25/05; converted to U.S. Patent Application, 10/25/06, Assigned to University of Kansas.
36. Kuehn F.E., Santos A.M., Herrmann W.A. Organorhenium (VII) and organomolybdenum (VI) oxides: Syntheses and application in olefin epoxidation. Dalton Trans. 2005, 2483.
37. Herrmann W.A., Kuehn F.E. Organorhenium Oxides. Acc. Chem. Res. 1997, 30:169.
38. Beattie R., Jones P.J. Methyltrioxorhenium. An air-stable compound containing a carbon-rhenium bond. Inorg. Chem. 1979, 18:2318.
39. Herrmann W.A., Fischer R.W., Rauch M.U., Scherer W. Multiple bonds between main-group elements transition metals. 125. Alkylrhenium oxides as homogeneous epoxidation catalysts: Activity, selectivity, stability, deactivation. J. Mol. Catal. 1994, 86:243.
40. Herrmann W.A., Fischer R.W., Marz D.W. Multiple bonding between main-group elements transition metals. 100. Part 2, Methyltrioxorhenium as catalyst for olefin oxidation. Angew. Chem. Int. Ed. Engl. 1991, 30:1638.
41. Kühn F.E., Santos A.M., Herrmann W.A. Organorhenium(VII) and organomolybdenum(VI) oxides: Syntheses and application in olefin epoxidation. J. Chem. Soc., Dalton Trans. 2005, 2483.
42. Kühn F.E., Herrmann W.A. Methyltrioxorhenium(VII) as an oxidation catalyst. Aqueous Phase Organometallic Catalysis 2004, 488. Wiley-VCH Verlag GmbH & Co, KGaA, Weinheim. 2nd ed. B. Cornils, W.A. Herrmann (Eds.).
43. Kühn F.E., Herrmann W.A. Organorhenium Oxides. Acc. Chem. Res. 1997, 30:169.
44. Espenson J.B., Abu-Omar M.M. Reactions catalyzed by methylrheniumtrioxide. Adv. Chem. Ser. 1997, 253:99. American Chemistry Society, Washington, DC.
45. Espenson J.H. Atom-transfer reactions catalyzed by methyltrioxorhenium(VII) - mechanisms and applications. Chem. Commun. 1999, 479.
46. Rudolph J., Reddy K.L., Chiang J.P., Sharpless K.B. Highly efficient epoxidation of olefins using aqueous H2O2 and catalytic Methyltrioxorhenium/pyridine; Pyridine-mediated ligand acceleration. J. Am. Chem. Soc. 1997, 119:6189.
47. Abu-Omar M.M., Hansen P.J., Espenson J.H. Deactivation of Methylrhenium trioxide-peroxide catalysts by diverse and competing pathways. J. Am. Chem. Soc. 1996, 118:4966.
48. Shu Z., Espenson J.H. Kinetics and mechanism of oxidation of anilines by hydrogen peroxide as catalyzed by Methylrhenium trioxide. J. Org. Chem. 1995, 60:1326.
49. Wang W.D., Espenson J.H. Thermal and photochemical reactions of methylrhenium diperoxide: Formation of methyl hydroperoxide in acetonitrile. Inorg. Chem. 1997, 36:5069.
50. Abu-Omar M.M., Espenson J.H. Oxidations of ER3 (E = P, As, or Sb) by hydorgen peroxide: Methylrhenium trioxide as catalyst. J. Am. Chem. Soc. 1995, 117:272.
51. Wang W.D., Espenson J.H. Effects of pyridine and its derivatives on the equilibria and kinetics pertaining to epoxidation reactions catalyzed by methyltrioxorhenium. J. Am. Chem. Soc. 1998, 120:11335.
52. Yamazaki S., Espenson J.H., Huston P. Equilibria and kinetics of the reactions between hydrogen peroxide and methyltrioxorhenium in aqueous perchloric acid solutions. Inorg. Chem. 1993, 32:4683.
53. Hansen P.J., Espenson J.H. Oxidation of chloride ions by hydrogen peroxide, catalyzed by methylrhenium trioxide. Inorg. Chem. 1995, 34:5839.
54. Coperet C., Adolfsson H., Sharpless K.B. A simple and efficient method for epoxidation of terminal alkenes. J. Chem. Soc. Chem. Commun. 1997, 1565.
55. Herrmann W.A., Kratzer R.M., Kuhn F.E., Haider J.J., Fischer R.W. Multiple bonds between transition metals and main-group elements. Part 168. Methyltrioxorhenium/Lewis base catalysts in olefin epoxidation. J. Organomet. Chem. 1997, 549:319.
56. Nam W., Ho R., Valentine J.S. Iron-cyclam complexes as catalysts for the epoxidation of olefins by 30% aqueous hydrogen peroxide in acetonitrile and methanol. J. Am. Chem. Soc. 1991, 113:7052.
57. Vaz D.N., McGinnity D.F., Coon M.J. Epoxidation of olefins by cytochrome P450: Evidence from site-specific mutagenesis for hydroperoxo-iron as an electrophilic oxidant. Proc. Natl. Acad. Sci. USA 1998, 95:3555.
58. Avila L., Huang H., Damaso C.O., Lu S., Moënne-Loccoz P., Rivera M. Coupied oxidation vs heme oxygenation: Insights from axial ligand mutants of mitochondrial cytochrome b5. J. Am. Chem. Soc. 2003, 125:4103.
59. Nam W., Lim M.H., Lee H.J., Kim C. Evidence for the participation of two distinct reactive intermediates in Iron(III) porphyrin complex-catalyzed epoxidation reactions. J. Am. Chem. Soc. 2000, 122:6641.
60. Newcomb M., Aebisher D., Shen R., Chandrasena R.E.P., Hollenberg P.F., Coon M.J. Kinetic isotope effects implicate two electrophilic oxidants in cytochrome P450-Catalyzed hydroxylations. J. Am. Chem. Soc. 2003, 125:6064.
61. Toy P.H., Newcomb M., Coon M.J., Vaz A.D.N. Two distinct electrophilic oxidants effect hydroxylation in cytochrome P-450-catalyzed reactions. J. Am. Chem. Soc. 1998, 120:9718.
62. Sam J.W., Tang X.J., Peisach J. Electrospray mass spectrometry of iron Bleomycin: Demonstration that activated Bleomycin is ferric peroxide complex. J. Am. Chem. Soc. 1994, 116:5250.
63. Ho R.Y.N., Roelfes G., Feringa B.L., Que L. Raman evidence for a weakened O-O bond in mononuclear low-spin Iron(III)-hydroperoxides. J. Am. Chem. Soc. 1999, 121:264.
64. Lubben M., Meetsma A., Wilkinson E.C., Feringa B., Que L. Nonheme iron centers in oxygen activation: Characterization of an iron(III) hydroperoxide intermediate. Angew. Chem. Int. Ed. Engl. 1995, 34:1512.
65. Collman J.P., Zeng L., Brauman J.I. Donor ligand effect on the nature of the oxygenating species in MnIII(salen)-catalyzed epoxidation of olefins: Experimental evidence for multiple active oxidants. Inorg. Chem. 2004, 43:2672.
66. VanAtta R.B., Franklin C.C., Valentine J.S. Oxygenation of organic substrates by iodosylbenzene catalyzed by soluble manganese, iron, cobalt, or copper salts in acetonitrile. Inorg. Chem. 1984, 23:4121.
67. Wang S.H., Mandimutsira B.S., Todd R., Ramdhanie B., Fox J.P., Goldberg D.P. Catalytic Sulfoxidation and Epoxidation with a Mn(III) Triazacorrole: Evidence for a "Third Oxidant" in high-valent porphyrinoid oxidations. J. Am. Chem. Soc. 2004, 126:18.
68. Hubin T.J., McCormick J.M., Collinson S.R., Buchalova M., Perkins C.M., Alcock N.W., Kahol P.K., Raghunathan A., Busch D.H. New Iron(II) and Manganese(II) complexes of two ultra-rigid, cross-bridged tetraazamacrocycles for catalysis and biomimicry. J. Am. Chem. Soc. 2000, 122:2512.
69. Busch D.H., Collinson S.R., Hubin T.J. Catalysts and methods for catalytic oxidation Sept. 11, 1998, WO 98/39098, Assigned to University of Kansas.
70. Busch D.H., Collinson S.R., Hubin T.J., Labeque R., Williams B.K., Johnston J.P., Kitko D., Burckett-St.Laurent J., Perkins C.M. Bleach compositions Sept. 11, 1998, WO 98/39406, Assigned to Procter and Gamble Company.
71. Garrison J.M., Bruice T.C. Intermediates in the epoxidation of alkenes by cytochrome P-450 models. 3. Mechanism of oxygen transfer from substituted oxochromium(V) porphyrins to olefinic substrates. J. Am. Chem. Soc. 1989, 111:191.
72. Collman J.P., Chien A.S., Eberspacher T.A., Brauman J.I. Multiple active oxidants in cytochrome P-450 model oxidations. J. Am. Chem. Soc. 2000, 122:11098.
73. Zhang W., Jacobsen E.N. Asymmetric olefin epoxidation with sodium hypochlorite catalyzed by easily prepared chiral manganese(III) salen complexes. J. Org. Chem. 1991, 56:2296.
74. Yin G., McCormick J.M., Buchalova M., Danby A.M., Rodgers K., Smith K., Perkins C., Kitko D., Carter J., Scheper W.M., Busch D.H. Synthesis, characterization, and solution properties of a novel cross-bridged cyclam Manganese(IV) complex having two terminal hydroxo ligands. Inorg. Chem. 2006, 45:8052.
75. Bordwell F.G., Cheng J.P., Harrelson J.A. Homolytic bond dissociation energies in solution from equilibrium acidity and electrochemical data. J. Am. Chem. Soc. 1988, 110:1229.
76. Mayer J.M. Hydrogen atom abstraction by metal-oxo complex: Understanding the analogy with organic radical reations. Acc. Chem. Res. 1998, 37:441.
77. Yin G., Danby A.M., Kitko D., Carter J.D., Scheper W.M., Busch D.H. Understanding the selectivity of a moderate oxidation catalyst. Hydrogen abstraction by a fully characterized activated catalyst, the robust dihydroxo Manganese(IV) complex of a bridged cyclam. J. Am. Chem. Soc. 2007, 129:1512.
78. Yin G., Buchalova M., Danby A.M., Perkins C.M., Kitko D., Carter J.D., Scheper W.M., Busch D.H. Olefin oxygenation by the hydroperoxide adduct of a nonheme Manganese(IV) complex: Epoxidations by a metallo-peracid produces gentle selective oxidations. J. Am. Chem. Soc. 2005, 127:17170.
79. Yin G., Buchalova M., Danby A.M., Perkins C.M., Kitko D., Carter J.D., Scheper W.M., Busch D.H. Olefin epoxidation by the hydrogen peroxide adduct of a novel non-heme Manganese(IV) complex: Demonstration of oxygen transfer by multiple mechanisms. Inorg. Chem. 2006, 45:3467.
80. Yin G., Danby A.M., Kitko D., Carter J.D., Scheper W.M., Busch D.H. Olefin epoxidation by alkyl hydroperoxide with a novel cross-bridged cyclam manganese complex: Demonstration of oxygenation by two distinct reactive intermediates. [Erratum to document cited in CA146:316400]. Inorg. Chem. 2007, 46:2173.
81. He G., Bruice T.C. The rate-limiting step in the one-electron oxidation of an alkene by oxo[meso-tetrakis(2,6-dibromophenyl)porphinato]chromium(V) is the formation of a charge-transfer complex. J. Am. Chem. Soc. 1991, 113:2747.
82. Meunier B., Guilmet E., De Carvalho M., Poilblanc R. Sodium hypochlorite: A convenient oxygen source for olefin epoxidation catalyzed by (porphyrinato)manganese complexes. J. Am. Chem. Soc. 1984, 106:6668.
83. Battioni P., Renaud J.P., Bartoli J.F.M., Reina-Artiles M., Fort M., Mansuy D. Monooxygenase-like oxidation of hydrocarbons by hydrogen peroxide catalyzed by manganese porphyrins and imidazole: Selection of the best catalytic system and nature of the active oxygen species. J. Am. Chem. Soc. 1988, 110:8462.
84. Collman J.P., Lee V.J., Kellen-Yuen C.J., Zhang X., Ibers J.A., Brauman J.I. Threitol-strapped manganese porphyrins as enantioselective epoxidation catalysts of unfunctionalized olefins. J. Am. Chem. Soc. 1995, 117:692.
85. Murphy A., Bubois G., Stack T.D.P. Efficient epoxidation of electron-deficient olefins with a cationic manganese complex. J. Am. Chem. Soc. 2003, 125:5250.
86. Groves J.T., Stern M.K. Synthesis, characterization, and reactivity of oxomanganese(IV) porphyrin complexes. J. Am. Chem. Soc. 1988, 110:8628.
87. Arasasingham R., He G., Bruice T.C. Mechanism of manganese porphyrin-catalyzed oxidation of alkenes. Role of manganese(IV)-oxo species. J. Am. Chem. Soc. 1993, 115:7985.
88. Bernadou J., Fabiano A., Robert A., Meunier B. Redox tautomerism in high-valent metal-oxo-aquo complexes.Origin of the oxygen atom in epoxidation reactions catalyzed by water-soluble metalloporphyrins. J. Am. Chem. Soc. 1994, 116:9375.
89. Groves J.T., Lee J., Marla S.S. Detection and characterization of an oxomanganese(V) porphyrin complex by rapid-mixing Stopped-flow spectrophotometry. J. Am. Chem. Soc. 1997, 119:6269.
90. Caudle M.T., Riggs-Gelasco P., Gelasco A.K., Penner-Hahn J.E., Pecoraro V.L. Mechanism for the homolytic cleavage of alkyl hydroperoxides by the Manganese(III) dimer MnIII2(2-OHsalph)2. Inorg. Chem. 1996, 35:3577.
91. Deubel D.V., Frenking G., Gisdakis P.J., Herrmann W.A., Rösch N., Sundermeyer J. Olefin epoxidation with inorganic peroxides. Solutions to four long-standing controversies on the mechanism of oxygen transfer. Acc. Chem. Res. 2004, 37:645.
92. Groves J.T., Lee J., Marla S.S. Detection and characterization of an Oxomanganese(V) Porphyrin complex by rapid mixing stopped-flow spectrophotometry. J. Am. Chem. Soc. 1997, 119:6269.
93. Ostovic D., Bruice T.C. Mechanism of alkene epoxidation by iron. chromium and manganese higher valent oxo-metalloporphyrins. Acc. Chem. Res. 1992, 25:314.
94. Katsuki T., Sharpless K.B. The first practical method for asymmetric epoxidation. J. Am. Chem. Soc. 1980, 102:5974.
95. Chaumette P., Mimoun H., Saussine L., Fischer J., Mitachler A. Peroxo and alkylperoxidic molybdinum(V), complexes as intermediates in the epoxidation of olefins by alkyl hydroperoxides. J. Organomet. Chem. 1983, 250:291.
96. Herrmann W.A., Kratzer R.M., Ding H., Thiel W., Glas H. Methyltrioxorhenium/pyrazole a highly efficient calayst in the epoxidation of olefins. J. Organomet. Chem. 1998, 555:293.
97. Vrettos J.S., Brudvig G.W. Oxygen evolution. Comprehensive Coordination Chemistry II 2004, Vol. 8:507-547. Elsevier.
98. Tommos C., Babcock G.T. Oxygen production in nature: A light-driven metalloradical enzyme process. Acc. Chem. Res. 1998, 31:18.
99. Brill W.F. The origin of epoxides in the liquid phase oxidation of olefins with molecular oxygen. J. Am. Chem. Soc. 1984, 85:141.
100. Adam W., Roschmann K.J., Saha-Möller C.R., Seebach D. cis-Stilbene and (1a,2b,3a)-(2-Ethenyl-3-methoxycyclopropyl)benzene as mechanistic probes in the MnIII(salen)-catalyzed epoxidation: Influence of the oxygen source and the counterion on the diastereoselectivity of the competitive concerted and radical-type oxygen transfer. J. Am. Chem. Soc. 2002, 124:5068.
101. Dean J.A. Lange's Handbook of Chemistry 1973, 4-32. McGraw-Hill, New York, NY. 4th ed.
102. Lee H.-J., Shi T.P., Busch D.H., Subramaniam B. A greener pressure intensified propylene epoxidation process with facile product separation. Chem. Eng. Sci. 2007, 62:7282.