Skip to main content
SpringerLink
Log in

Catalytic oxidations using ruthenium porphyrins

  • Chapter
Advances in Catalytic Activation of Dioxygen by Metal Complexes

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 26))

Abstract

The major goal of the Chapter is to review developments in the use of Ru-porphyrin complexes as homogeneous (or matrix-supported) catalysts for oxygenation and oxidation processes. The subject was given impetus with the discovery of a remarkable reaction in which a Ru(II) porphyrin complex reacted with O2 to give a trans-dioxo-Ru(VI) species. Such species, which can be formed from a wide range of O-atom donors, were shown subsequently to be capable of acting as a bis(monooxygenase) in transferring both the coordinated oxo ligands (as O-atoms) to olefinic substrates, saturated hydrocarbons, phosphines, and thioethers, and the processes become catalytic in the presence of excess of the O-atom donor. Further, the dioxo species can also exhibit oxidase-like activity, and effect stoichiometric or catalytic oxidative-dehydrogenation of phenols, alkoxyarenes, alcohols, and amines. Use of chiral porphyrins has led to catalytic, asymmetric epoxidation and hydroxylations, even though radical intermediates are invoked, as well as oxygenation of racemic substrates (phosphines and more interestingly tertiary alkanes) to yield chiral products by kinetic resolution processes. The reaction mechanisms invoked range from genuine O-atom transfer (from RuVI, RuV, or RuIV species, where the disproportionation reaction [2 O=RuIV⇋RuII+O=RuVI=O] is important), to free-radical induced processes, particularly when the porphyrin ligands are extensively halogenated, as Ru complexes generally of such porphyrins are extremely active in radical-type decomposition of hydroperoxides, often present as trace impurities in hydrocarbon substrates.

The amine dehydrogenation chemistry has led to characterization of Ru-imine, -imido (i.e. nitrene), -oxo(imido), -amido, as well as -amine complexes, the types of species that are intermediates in some reductive enzyme processes, and in reactions such as oxyamination, amination, and aziridination; the last mentioned process involves transfer of the imido moiety (isoelectronic with the oxo group), and corresponding catalytic aziridination of alkenes and insertion of the imido group into alkanes to give amides can be catalyzed by Ru-porphyrin complexes; with chiral porphyrins, chiral recognition in binding of racemic aminoesters has been realized and enantioeselective amidation of hydrocarbon substrates has been demonstrated.

The beginning of the Chapter gives a general introduction to catalyzed oxygenation/oxidation reactions involving O2, and briefly describes enzymatic oxygenase and oxidase systems, particularly the monooxygenase, cytochrome P-450, as the attempted modelling of this system using Ru-porphyrin complexes led to the discovery of the trans-dioxo-Ru(VI) species and their chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. For a general introduction to O2-oxidations see (a) James, B.R. Adv. Chem. Ser., 1980, 191, 253. (b) Sheldon, R.A.; Kochi, J.K. Metal-Catalyzed Oxidation of Organic Compounds; Academic Press: New York, 1981. (c) Simandi, L. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Dordrecht, 1992. (d) Barton, D.H.R.; Martell, A.E.; Sawyer, D.T. (eds.). The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Plenum Press: New York, 1993.

    CAS  Google Scholar 

  2. Funabiki, T. Oxygenases and Model Systems; Kluwer Academic Publishers: Dordrecht, 1997. See also Chapter in this present volume.

    Google Scholar 

  3. Lippard, S.J.; Berg, J.M. Principles of Bioinorganic Chemistry; University Science Books: Mill Valley, CA, p. 317, 1994.

    Google Scholar 

  4. Sono, M.; Roach, M.P.; Coulter, E.D.; Dawson, J.H. Chem. Rev., 1996, 96, 2841.

    Article  CAS  Google Scholar 

  5. Dickerson, R.E.; Geiss, I. Hemoglobin: Structure, Function, Evolution, and Pathology; Benjamin/Cummings: Menlo Park, 1983. (b) Ref. 3, Ch. 11.

    Google Scholar 

  6. Martell, A.E.; Sawyer, D.T. (eds.). Oxygen Complexes and Oxygen Activation by Transition Metals; Plenum Press: New York, 1988.

    Google Scholar 

  7. Groves, J.T.; McMurry, T.J. Cytochrome P-450: Structure, Mechanism and Biochemistry; (Oritz de Montellano ed.); Plenum Press: New York, Ch. 1, 1986. (b) Groves, J.T. J. Chem. Educ., 1985, 62, 928.

    Google Scholar 

  8. James, B.R. in Fundamental Research in Homogeneous Catalysis; (Shilov, A.E. ed.); Gordon & Breach: New York, Vol. 1, p. 309, 1986.

    Google Scholar 

  9. Sheldon, R.A. in Metalloporphyrins in Catalytic Oxidations; (Sheldon, R.A. ed.); Marcel Dekker Inc.: New York, Ch. 1, 1994. See also Chapter in this present volume.

    Google Scholar 

  10. Moro-oka, Y.; Akita, M. Catal. Today, 1998, 41, 327.

    Article  CAS  Google Scholar 

  11. Mansuy, D.; Battioni, P. in Metalloporphyrins in Catalytic Oxidations; (Sheldon, R.A. ed.); Marcel Dekker Inc.: New York, Ch. 4, 1994. (b) Mansuy, D. Pure Appl. Chem., 1987, 59, 759.

    Google Scholar 

  12. Tabushi, I. Coord. Chem. Rev., 1988, 86, 1.

    Article  CAS  Google Scholar 

  13. Bruice, T.C. Aldrichim. Acta, 1988, 21, 87.

    CAS  Google Scholar 

  14. Meunier, B. Chem. Rev., 1992, 92, 1411. (b) Meunier, B.; Robert, A.; Pratviel, G.; Bernadou, J. in The Porphyrin Handbook; (Kadish, K.M.; Smith, K.M.; Guilard, R. eds.); Academic Press: San Diego, CA, Vol. 4, Ch. 31, 2000.

    Article  CAS  Google Scholar 

  15. James, B.R. Chem. Ind. (Marcel Dekker) 1992, 47, 245. (b) Mlodnicka, T.; James, B.R. in Metalloporphyrin Catalyzed Oxidations; (Montanari, F.; Casella, L. eds.); Kluwer Academic Publishers: Dordrecht, p. 121, 1994.

    CAS  Google Scholar 

  16. Raag, R.; Poulos, T.L. Biochemistry, 1991, 30, 2674. (b) Poulos, T.L. in The Porphyrin Handbook; (Kadish, K.M.; Smith, K.M.; Guilard, R. eds.); Academic Press: San Diego, CA, Vol. 4, Ch. 32, 2000. (c) Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A.M.; Maves, S.A.; Benson, D.E.; Sweet, R.M.; Ringe, D.; Petsko, G.A.; Sligar, S.G. Science, 2000, 287, 1615.

    CAS  Google Scholar 

  17. Mashiko, T.; Reed, C.A.; Haller, V.; Scheidt, W.R. Inorg Chem., 1984, 23, 3192.

    Article  CAS  Google Scholar 

  18. Tabushi, I.; Yazaki, A. J. Am. Chem. Soc., 1981, 103, 7371.

    CAS  Google Scholar 

  19. Perrée-Fauvet, M.; Gaudemer, A. J. Chem. Soc., Chem. Commun., 1981, 874.

    Google Scholar 

  20. Aoyama, Y.; Watanabe, T.; Onda, H.; Ogoshi, H. Tetrahedon Lett., 1983, 24, 1183.

    CAS  Google Scholar 

  21. Mansuy, D.; Fontecave, M.; Bartoli, J.F. J. Chem. Soc., Chem. Commun., 1983, 253.

    Google Scholar 

  22. Shimizu, M.M.; Orita, H.; Hayakawa, T.; Takehira, K. J. Mol. Catal., 1988, 45, 85.

    CAS  Google Scholar 

  23. Barton, D.H.R.; Doller, D. Acc. Chem. Res., 1992, 25, 504.

    Article  CAS  Google Scholar 

  24. Tabushi, I.; Kodera, M.; Yokoyama, M. J. Am. Chem. Soc., 1985, 107, 4466.

    CAS  Google Scholar 

  25. Fontecave, M.; Mansuy, D. Tetrahedron, 1984, 40, 4297.

    Article  CAS  Google Scholar 

  26. Battioni, P.; Bartoli, J.F.; Leduc, P.; Fontecave, M.; Mansuy, D. J. Chem. Soc., Chem. Commun., 1987, 791.

    Google Scholar 

  27. Karasevich, F.I.; Khenkin, A.M.; Shilov, A.E. J. Chem. Soc., Chem. Commun., 1987, 731.

    Google Scholar 

  28. Khenkin, A.M.; Shilov, A.E. New J. Chem., 1989, 13, 659.

    CAS  Google Scholar 

  29. Shulpin, G.B.; Druzhinina, A.N. Izv. Acad. Nauk SSSR, Ser Khim., 1991, 12, 2739.

    Google Scholar 

  30. Creager, S.E.; Raybuck, S.A.; Murray, R.W. J. Am. Chem. Soc., 1986, 108, 4225.

    Article  CAS  Google Scholar 

  31. Mlodnicka, T. in Metalloporphyrins in Catalytic Oxidations; (Sheldon, R.A. ed.); Marcel Dekker Inc.: New York, Ch. 9, 1994. (b) Mlodnicka, T. J. Mol. Catal., 1986, 36, 205.

    Google Scholar 

  32. Ostovic, D.; Bruice, T.C. Acc. Chem. Res., 1992, 25, 314.

    Article  CAS  Google Scholar 

  33. Robert, A.; Meunier, B. New J. Chem., 1988, 12, 855.

    Google Scholar 

  34. James, B.R.; Addison, A.W.; Cairns, M.; Dolphin, D.; Farrell, N.P.; Paulson, D.R.; Walker, S. in Fundamental Research in Homogeneous Catalysis; (Tsutsui, M. ed.); Plenum Press: New York, Vol. 3, p. 751, 1979. (b) James, B.R. in The Porphyrins; (Dolphin, D. ed.); Academic Press: New York, Vol. 4, Ch. 6, 1978.

    Google Scholar 

  35. Jones, B.D.; Summerville, D.A.; Basolo, F. Chem. Rev., 1979, 79, 139.

    Article  CAS  Google Scholar 

  36. Walker, F.A.; Beroiz, D.; Kadish, K.M. J. Am. Chem. Soc., 1976, 98, 3484. (b) Stynes, D.V.; Stynes, H.C.; Ibers, J.A.; James, B.R. J. Am. Chem. Soc., 1973, 95, 1142 and 4087.

    CAS  Google Scholar 

  37. Wayland, B.B.; Newmann, A.R. J. Am. Chem. Soc., 1979, 101, 6472.

    Article  CAS  Google Scholar 

  38. James, B.R.; Stynes, D.V. J. Am. Chem. Soc., 1972, 94, 6225.

    Article  CAS  Google Scholar 

  39. Che, C.-M.; Yu, W.-Y. Pure Appl. Chem., 1999, 71, 281.

    CAS  Google Scholar 

  40. Groves, J.T.; Shalyaev, K.; Lee, J. in The Porphyrin Handbook; (Kadish, K.M.; Smith, K.M.; Guilard, R. eds.); Academic Press: San Diego, CA, Vol. 4, Ch. 26, 2000. (b) Groves, J.T. Proc. 8th Intern. Symp. on Homog. Catal., Amsterdam, 1992, Lecture K-6.

    Google Scholar 

  41. Griffith, W.P. Chem. Rev., 1992, 21, 179.

    CAS  Google Scholar 

  42. Murahashi, S.I.; Oda, Y.; Naota, T. J. Am. Chem. Soc., 1992, 114, 7914.

    Article  Google Scholar 

  43. Gore, E.S. Plat. Met. Rev., 1983, 27, 111.

    CAS  Google Scholar 

  44. da Silva, J.J.R.F.; Williams, R.J.P. The Biological Chemistry of the Elements; Claredon Press: Oxford, Ch. 15, 1991. (b) Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistry of Life; John Wiley & Sons: New York, Ch. 10, 1994. (c) Solomon, E.I.; Sundaram, U.M.; Machonkin, T.E. Chem. Rev., 1996, 96, 2563.

    Google Scholar 

  45. Gentschev, P.; Möller, N.; Krebs, B. Inorg. Chim. Acta, 2000, 300–302, 442.

    Google Scholar 

  46. Ito, N.; Knowles, P.F.; Phillips, S.E.V. Methods Enzymol., 1995, 258, 235.

    CAS  Google Scholar 

  47. Rogers, M.S.; Knowles, P.F.; Baron, A.J.; McPherson, M.J.; Dooley, D.M. Inorg. Chim. Acta, 1998, 275–276, 175.

    Google Scholar 

  48. Chapman, S.K. in Perspectives in Bioinorganic Chemistry; (Hay, R.W.; Dilworth, J.R.; Nolan, K.B. eds.); JAI Press: London, Vol. 1, p. 95, 1991. (b) Ref. 3 p. 237.

    Google Scholar 

  49. Ke, M.; Sishta, C.; James, B.R.; Dolphin, D.; Sparapany, J.W. Inorg Chem., 1991, 30, 4766.

    Article  CAS  Google Scholar 

  50. Farrell, N.P.; Dolphin, D.; James, B.R. J. Am. Chem. Soc., 1978, 100, 324.

    Article  CAS  Google Scholar 

  51. Paulson, D.R.; Addison, A.W.; Dolphin, D.; James, B.R. J. Biol. Chem., 1979, 254, 7002.

    CAS  Google Scholar 

  52. James, B.R. Stud. Surface Sci. Catal., 1991, 66, 195.

    CAS  Google Scholar 

  53. Collman, J.P.; Barnes, C.E.; Brothers, P.J.; Collins, T.J.; Ozawa, T.; Gallucci, J.C.; Ibers, J.A. J. Am. Chem. Soc., 1984, 106, 5151.

    CAS  Google Scholar 

  54. Barringer Jr., L.F.; Rillema, D.P.; Ham, J.H. J. Inorg. Biochem., 1984, 21, 195.

    Article  CAS  Google Scholar 

  55. Collman, J.P.; Brauman, J.I.; Fitzgerald, J.P.; Sparapany, J.W.; Ibers, J.A. J. Am. Chem. Soc., 1988, 110, 3486.

    CAS  Google Scholar 

  56. Paeng, I.R.; Nakamoto, K. J. Am. Chem. Soc., 1990, 112, 3289.

    Article  CAS  Google Scholar 

  57. James, B.R.; Mikkelsen, S.R.; Leung, T.W.; Williams, G.H.; Wong, R. Inorg. Chim. Acta, 1984, 85, 209.

    Article  CAS  Google Scholar 

  58. Collman, J.P.; Barnes, C.E.; Sweptson, P.N.; Ibers, J.A. J. Am. Chem. Soc., 1994, 106, 3500.

    Google Scholar 

  59. Camenzind, M.J.; James, B.R.; Dolphin, D. J. Chem. Soc., Chem. Commun., 1986, 1137.

    Google Scholar 

  60. Groves, J.T.; Quinn, R. J. Am. Chem. Soc., 1985, 107, 5790.

    CAS  Google Scholar 

  61. Groves, J.T.; Ann, K.-H. Inorg. Chem., 1987, 26, 3831.

    CAS  Google Scholar 

  62. Sishta, C.; Ke, M.; James, B.R.; Dolphin, D. J. Chem. Soc., Chem. Commun., 1986, 787.

    Google Scholar 

  63. Cheng, S.Y.S.; James, B.R. J. Mol. Catal., 1997, 117, 91.

    Article  CAS  Google Scholar 

  64. Groves, J.T.; Quinn, R. Inorg. Chem., 1984, 23, 3844.

    Article  CAS  Google Scholar 

  65. Cheng, S.Y.S. Ph.D. Dissertation, University of British Columbia, Vancouver, 1996.

    Google Scholar 

  66. Leung, W.-H.; Che, C.-M.; Yeung, C.-H.; Poon, C.-K. Polyhedron, 1993, 12, 2331.

    CAS  Google Scholar 

  67. Leung, W.-H.; Che, C.-M. J. Am. Chem. Soc., 1989, 111, 8812.

    Article  CAS  Google Scholar 

  68. Huang, J.-S.; Che, C.-M.; Poon, C.-K. J. Chem. Soc., Chem. Commun., 1992, 161.

    Google Scholar 

  69. Dolphin, D.; James, B.R.; Leung, T. Inorg. Chim. Acta, 1983, 79, 25. (b) Leung, T.W.; James, V.; Dolphin, D. ibid. 1983, 79, 180.

    Article  Google Scholar 

  70. Barley, M.; Becker, J.Y.; Domazetis, G.; Dolphin, D.; James, B.R. Can. J. Chem., 1983, 61, 2389.

    CAS  Google Scholar 

  71. Sishta, C. Ph. D. Dissertation, University of British Columbia, Vancouver, 1990.

    Google Scholar 

  72. Balch, A.L.; Latos-Grazynski, L.; Renner, M.W. J. Am. Chem. Soc., 1985, 107, 2983.

    CAS  Google Scholar 

  73. Yamaguchi, K.; Watanabe, Y.; Morishima, I. J. Chem. Soc., Chem. Commun., 1992, 1721.

    Google Scholar 

  74. Rajapakse, N.; James, B.R.; Dolphin, D. Stud. Surface Sci. Catal., 1990, 55, 109.

    Google Scholar 

  75. Masuda, H.; Taga, T.; Osaki, K.; Sugimoto, H.; Mori, M.; Ogoshi, H. J. Am. Chem. Soc., 1981, 103, 2199.

    Article  CAS  Google Scholar 

  76. Camenzind, M.J.; James, B.R.; Dolphin, D.; Sparapany, J.W.; Ibers, J.A. Inorg. Chem., 1988, 27, 3054.

    Article  CAS  Google Scholar 

  77. Rajapakse, N.; James, B.R.; Dolphin, D. Can. J. Chem., 1990, 68, 2274.

    CAS  Google Scholar 

  78. Pacheco-Olivella, A.A. Ph. D. Dissertation, University of British Columbia, Vancouver, 1992.

    Google Scholar 

  79. Sishta, C.; James, B.R. unpublished results.

    Google Scholar 

  80. Sishta, C.; Camenzind, M.J.; James, B.R.; Dolphin, D. Inorg. Chem., 1987, 26, 1181.

    CAS  Google Scholar 

  81. Roecker, L.; Dobson, J.C.; Vining, W.J.; Meyer, T.J. Inorg. Chem., 1987, 26, 779.

    Article  CAS  Google Scholar 

  82. Le Maux, P.; Bahri, H.; Simonneaux, G. J. Chem. Soc., Chem. Commun., 1994, 1287.

    Google Scholar 

  83. Le Maux, P.; Bahri, H.; Simonneaux, G.; Toupet, L. Inorg. Chem., 1995, 34, 4691.

    Google Scholar 

  84. Groves, J.T.; Han, Y.; Engen, D.V. J. Chem. Soc., Chem. Commun., 1990, 436.

    Google Scholar 

  85. Holm, R.H.; Donahue, J.P. Polyhedron, 1993, 12, 571.

    Article  CAS  Google Scholar 

  86. Riley, D.P.; Smith, M.R.; Correa, P.E. J. Am. Chem. Soc., 1988, 110, 177.

    Article  CAS  Google Scholar 

  87. Yang, Y.C.; Szafraniec, L.L.; Beaudry, W.T. J. Org. Chem., 1990, 55, 3664.

    Article  CAS  Google Scholar 

  88. Hill, C.L.; Gall, R.D. J. Mol. Catal., 1996, 114, 103.

    CAS  Google Scholar 

  89. Rajapakse, N.; James, B.R.; Dolphin, D. Catal. Lett., 1989, 2, 219.

    Article  CAS  Google Scholar 

  90. Yamaguchi, K.; Watanabe, Y.; Morishima, T. Inorg. Chem., 1993, 32, 329.

    Google Scholar 

  91. Ando, W.; Tajima, R.; Takata, T. Tetrahedron Lett., 1982, 23, 1685.

    CAS  Google Scholar 

  92. Ellis, P.E.; Lyons, J.E. Coord. Chem. Rev., 1990, 105, 181. (b) Ellis, P.E.; Lyons, J.E. Catal. Lett., 1989, 3, 389.

    Article  CAS  Google Scholar 

  93. Traylor, T.J.; Tsuchiya, S. Inorg. Chem., 1987, 26, 1338.

    Article  CAS  Google Scholar 

  94. Xie, L.Y.; Dolphin, D. in Metalloporphyrin Catalyzed Oxidations; (Montanari, F.; Casella, L. eds.); Kluwer Academic Publishers: Dordrecht, p. 269, 1994. (b) Dolphin, D.; Traylor, T.J.; Xie, L.Y. Acc. Chem. Res., 1997, 30, 251.

    Google Scholar 

  95. Rajapakse, N.; James, B.R unpublished results.

    Google Scholar 

  96. Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett., 1991, 32, 7435. (b) Higuchi, T.; Hirobe, M. J. Mol. Catal., 1996, 113, 403.

    Article  CAS  Google Scholar 

  97. James, B.R.; Pacheco, A.; Rettig, S.J.; Ibers, J.A. Inorg. Chem., 1988, 27, 2414.

    Article  CAS  Google Scholar 

  98. Pacheco, A.; James, B.R.; Rettig, S.J. Inorg. Chem., 1999, 38, 5579.

    Article  CAS  Google Scholar 

  99. Still, W.C. J. Am. Chem. Soc., 1979, 101, 2493. (b) Pirkle, W.H.; Rinaldi, P.L. J. Org. Chem., 1979, 44, 1025.

    Article  CAS  Google Scholar 

  100. Bartok, D.M.; Lang, K.L. in The Chemistry of Functional Groups, Supplement; (Patai, S. ed.); John Wiley & Sons: New York, p. 609, 1980.

    Google Scholar 

  101. Hill, C.L. in Activation and Functionalization of Alkanes; (Hill C.L. ed.), John Wiley & Sons: New York, Ch. 8, 1989.

    Google Scholar 

  102. Alexander, C.; James, B.R. unpublished results.

    Google Scholar 

  103. Nam, W.; Valentine, J.S. J. Am. Chem. Soc., 1990, 112, 4977. (b) Sisemore, M.F.; Selke, M.; Burstyn, J.N.; Valentine, J.S. Inorg. Chem., 1997, 36, 979.

    Article  CAS  Google Scholar 

  104. Parshall, G.W.; Ittel, S.D. Homogeneous Catalysis; 2nd edn; John Wiley & Sons: New York, Ch. 6, 1992.

    Google Scholar 

  105. Groves, J.T.; Ahn, K.-H.; Quinn, R. J. Am. Chem. Soc., 1988, 110, 4217.

    CAS  Google Scholar 

  106. Scharbert, B.; Zeisberger, E.; Paulus, E. J. Organomet. Chem., 1995, 493, 143.

    Article  CAS  Google Scholar 

  107. Belani, R.M.; James, B.R.; Dolphin, D.; Rettig, S.J. Can. J. Chem., 1988, 66, 2072.

    CAS  Google Scholar 

  108. Seyler, J.W.; Fanwick, P.E.; Leidner, C.R. Inorg. Chem., 1992, 31, 3699.

    CAS  Google Scholar 

  109. Domazetis, G.; Tarpey, B.; Dolphin, D.; James, B.R. J. Chem. Soc., Chem. Commun., 1981, 939.

    Google Scholar 

  110. James, B.R. in Comprehensive Organometallic Chemistry; (Wilkinson, G.; Stone, F.G.A.; Abel, E.W. eds.); Pergamon Press: Oxford, Vol. 8, Ch. 51, 1982.

    Google Scholar 

  111. Jørgensen, K.A. in Metalloporphyrins in Catalytic Oxidations; (Sheldon, V. ed.); Marcel Dekker Inc.: New York, Ch. 3, 1994.

    Google Scholar 

  112. Marchon, J.C.; Ramasseul, R. J. Chem. Soc., Chem. Commun., 1988, 298.

    Google Scholar 

  113. Marchon, J.C.; Ramasseul, R. J. Mol. Catal., 1989, 51, 29.

    CAS  Google Scholar 

  114. Marchon, J.C.; Ramasseul, R. J. Synth. Org. Chem., 1989, No 5, 389.

    Google Scholar 

  115. Tavares, M.; Ramasseul, R.; Marchon, J.C. Catal. Lett., 1990, 4, 163.

    Article  CAS  Google Scholar 

  116. Tavares, M.; Ramasseul, R.; Marchon, J.C. Catal. Lett., 1991, 8, 245.

    Article  CAS  Google Scholar 

  117. Tavares, M.; Ramasseul, R.; Marchon, J.C.; Bachet, B.; Brassy, C.; Mornon, J.P. J. Chem. Soc., Perkin Trans. II, 1992, 1321.

    Google Scholar 

  118. Muto, T.; Umehara, J.; Masumori, H.; Miura, T.; Kimura, M. Chem. Pharm. Bull., 1985, 33, 4749.

    CAS  Google Scholar 

  119. Groves, J.T.; Neumann, R. J. Am. Chem. Soc., 1987, 109, 5045.

    CAS  Google Scholar 

  120. de Carvalho, M.E.; Meunier, B. New J. Chem., 1986, 10, 223.

    Google Scholar 

  121. Grinstaff, M.W.; Hill, M.G.; Labinger, J.L.; Gray, H.B. Science, 1994, 264, 1311.

    CAS  Google Scholar 

  122. Furenlid, L.R.; Renner, M.W.; Fajer, J. J. Am. Chem. Soc., 1990, 112, 8987.

    CAS  Google Scholar 

  123. Liu, C.J.; Yu, W.-Y.; Peng, S.-M; Mak, C.W.; Che, C.-M. J. Chem. Soc., Dalton Trans., 1998, 1805.

    Google Scholar 

  124. Birnbaum, E.R.; Labinger, J.A.; Bercaw, J.E.; Gray, H.B. Inorg. Chim. Acta, 1998, 270, 433.

    Article  CAS  Google Scholar 

  125. de Roch, I.S.; Balacaneau, J.C. Bull. Soc. Chim. Fr., 1964, 1393.

    Google Scholar 

  126. Ingold, K.U. Aldrichim. Acta, 1989, 22, 69.

    CAS  Google Scholar 

  127. Ittel, S.D. Homogeneous Catalysis; 2nd edn; John Wiley & Sons: New York, Ch. 6, 1992 Ref. 104, Ch. 10.

    Google Scholar 

  128. Hansen, C.B.; Hoogers, G.J.; Drenth, W. J. Mol. Catal., 1993, 79, 153.

    CAS  Google Scholar 

  129. Hansen, C.B.; Drenth, W. Catal. Lett., 1993, 20, 359.

    Article  CAS  Google Scholar 

  130. Hansen, C.B.; Agterberg, F.P.W.; van Eijndhoven, A.M.C.; Drenth, W. J. Mol. Catal., 1995, 102, 117.

    Article  CAS  Google Scholar 

  131. Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. J. Chem. Soc., Chem. Commun., 1998, 1583.

    Google Scholar 

  132. Groves, J.T.; Meyers, R.S. J. Am. Chem. Soc., 1983, 105, 5791. (b) Collman, J.P.; Zhang, X.; Lee, V.J.; Uffelman, E.S.; Brauman, J.I. Science, 1993, 261, 1404. (c) Halterman, R.L.; Jan, S.-T.; Nimmons, H.L.; Standlee, D.J.; Khan, M.S. Tetrahedron, 1997, 53, 11257.

    CAS  Google Scholar 

  133. Gross, Z.; Ini, S.; Kapon, M.; Cohen, S. Tetrahedron Lett., 1996, 37, 7325.

    Article  CAS  Google Scholar 

  134. Berkessel, A.; Frauenkron, M. J. Chem. Soc., Perkin Trans I, 1997, 2265.

    Google Scholar 

  135. Gross, Z.; Ini, S. J. Org. Chem., 1997, 62, 5514.

    CAS  Google Scholar 

  136. Lai, T.-S.; Kwong, H.-L.; Zhang, R.; Che, C.-M. J. Chem. Soc., Dalton Trans., 1998, 3559.

    Google Scholar 

  137. Gross, Z.; Ini, S. Inorg. Chem., 1999, 38, 1446.

    Article  CAS  Google Scholar 

  138. Gross, Z.; Ini, S. Org. Lett., 1999, 1, 2077.

    CAS  Google Scholar 

  139. Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. J. Chem. Soc., Chem. Commun., 1999, 409.

    Google Scholar 

  140. Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett., 1989, 30, 6545.

    Article  CAS  Google Scholar 

  141. Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett., 1992, 33, 2521.

    Article  CAS  Google Scholar 

  142. Groves, J.T.; Gross, Z.; Stern, M.K. Inorg. Chem., 1994, 33, 5065.

    Article  CAS  Google Scholar 

  143. Gross, Z.; Nimri, S. J. Am. Chem. Soc., 1995, 117, 8021.

    CAS  Google Scholar 

  144. Gross, Z. J. Biol. Inorg. Chem., 1996, 1, 368.

    CAS  Google Scholar 

  145. Ohtake, H.; Higuchi, T.; Hirobe, M. Heterocycles, 1995, 40, 869.

    Google Scholar 

  146. Higuchi, T. J. Gen. Org. Chem. (Yuki Gosei Kagaku Kyokaishi) Jpn., 1995, 53, 633.

    CAS  Google Scholar 

  147. Higuchi, T.; Hirobe, M. J. Organomet. Chem., 1996, 113, 403.

    CAS  Google Scholar 

  148. Groves, J.T.; Roman, J.S. J. Am. Chem. Soc., 1995, 117, 5594.

    CAS  Google Scholar 

  149. Yamada, T.; Hashimoto, K.; Kitaichi, Y.; Suzuki, K.; Ikeno, T. Chem. Lett., 2001, 268.

    Google Scholar 

  150. Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc.. Chem. Commun., 1997, 65.

    Google Scholar 

  151. Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem., 1998, 63, 7364.

    CAS  Google Scholar 

  152. Yu, X.-Q.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc., 2000, 122, 5337.

    CAS  Google Scholar 

  153. van der Made, A.W.; Smeets, J. W.; Nolter, R.J.M.; Drenth, W. J. Chem. Soc., Chem. Commun., 1983, 1204.

    Google Scholar 

  154. Beck, J.S.; Vartuli, J.C.; Roth, W.J.; Leonowicz, M.E.; Kresge, C.T.; Schmitt, K.D.; Chu, C.T.-W.; Olson, D.H.; Sheppard, E.W.; McCullen, S.B.; Higgins, J.B.; Schlenker, J.L. J. Am. Chem. Soc., 1992, 114, 10834.

    Article  CAS  Google Scholar 

  155. Dobson, J.C.; Seok, W.K.; Meyer, T.J. Inorg. Chem., 1986, 25, 1513.

    CAS  Google Scholar 

  156. Takagi, S.; Miyamoto, T. K. Inorg. Chim. Acta, 1990, 173, 215.

    Article  CAS  Google Scholar 

  157. French, R.R.; Holzer, P.; Leuenberger, M.G.; Woggon, W.-D. Angew. Chem. Int. Ed., 2000, 39, 1267.

    Article  CAS  Google Scholar 

  158. Caris-Veyrat, C.; Amiot, M.-J.; Ramasseul, R.; Marchon, J.C. New J. Chem., 2001, 25, 203.

    Article  CAS  Google Scholar 

  159. Stoop, R.M.; Bauer, C.; Setz, P.; Wörle, M.; Wong, T.Y.H.; Mezzatti, A. Organometallics, 1999, 18, 5691. (b) Maran, F.; Morvillo, A.; ďAlessandro, N.; Bressan, M. Inorg. Chim. Acta, 1999, 288, 122.

    Article  CAS  Google Scholar 

  160. Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc., 1992, 114, 10660.

    Article  CAS  Google Scholar 

  161. Shingaki, T.; Miura, K.; Higuchi, T.; Hirobe, M.; Nagano, T. J. Chem. Soc., Chem. Commun., 1997, 861.

    Google Scholar 

  162. Groves, J. T.; Bonchio, M.; Carofiglio, T.; Shalyaev, K. J. Am. Chem. Soc., 1996, 118, 8961.

    Article  CAS  Google Scholar 

  163. Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. J. Chem. Soc., Chem. Commun., 1999, 1791.

    Google Scholar 

  164. Dubourdeaux, P.; Tavarès, M.; Grand, A.; Ramasseul, R.; Marchon, J.C. Inorg. Chim. Acta, 1995, 240, 657.

    Article  CAS  Google Scholar 

  165. Seok, W.K.; Dobson, J.C.; Meyer, T.J. Inorg. Chem., 1988, 27, 3.

    Article  CAS  Google Scholar 

  166. Higuchi, T.; Satake, C.; Hirobe, M. J. Am. Chem. Soc., 1995, 117, 8879.

    Article  CAS  Google Scholar 

  167. Cheng, S.Y.S.; Rajapakse, N.; Rettig, S.J.; James, B.R. J. Chem. Soc., Chem. Commun., 1994, 2669.

    Google Scholar 

  168. Bailey, A.J.; Cheng, S.Y.S.; James, B.R.; Rettig, S.J. to be published.

    Google Scholar 

  169. Dobson, H.K. M.Sc. Dissertation, University of British Columbia, Vancouver, 1998.

    Google Scholar 

  170. Huang, J.-S.; Che, C.-M; Li, Z.Y.; Poon, C.W. Inorg. Chem., 1992, 31, 1313.

    CAS  Google Scholar 

  171. Tony, K.J.; Makadevan, V.; Rajaram, J.; Swamy, C.S. React. Kinet. Catal. Lett., 1997, 62, 105.

    CAS  Google Scholar 

  172. Behari, K., Narayan, H.; Shukla, R.S.; Gupta, K.C. Int. J. Chem. Kinet., 1984, 16, 195.

    Article  CAS  Google Scholar 

  173. Bressan, M.; Forti, L.; Ghelfi, F.; Morvillo, A. J. Mol. Catal., 1993, 79, 85.

    CAS  Google Scholar 

  174. Lee, D.G.; Congson, L.N. Can. J. Chem., 1990, 68, 1774.

    CAS  Google Scholar 

  175. Wang, Z.; Chandler, W.D.; Lee, D.G. Can. J. Chem., 1998, 76, 919.

    CAS  Google Scholar 

  176. Li, C.-K.; Che, C.-M.; Tong, W.-F.; Lai, T.-F. J. Chem. Soc., Dalton Trans., 1992, 813. (b) Che, C.-M.; Tang, W.-T.; Lee, W.-O.; Wong, K.-Y.; Lau, T.-C. J. Chem. Soc., Dalton Trans., 1992, 1551. (c) Che, C.-M.; Tang, W.-T.; Wong, W.-T.; Lai, T.-F. J. Am. Chem. Soc., 89, 111, 9048.

    Google Scholar 

  177. Roecker, L.; Meyer, T.J. J. Am. Chem. Soc., 1987, 109, 746.

    Article  CAS  Google Scholar 

  178. Gorrod, J.W. Biological Oxidation of Nitrogen; Elsevier/North Holland Biomedical Press: New York, 1978.

    Google Scholar 

  179. Silverman, R.B. The Organic Chemistry of Drug Design and Drug Action; Academic Press: San Diego, 1992.

    Google Scholar 

  180. Griffin, B.W.; Marth, C.; Yasukochi, Y.; Masters, B.S.S. Arch. Biochem. Biophys., 1980, 205, 403. (b) Shono, T.; Toda, T.; Oshino, N. J. Am. Chem. Soc., 1982, 104, 2639. (c) Janzowski, C.; Gottfried, J.; Preussman, R.; Eisenbrand, G. Carcinogenesis, 1985, 6, 79. (d) Goldblum, A.; Loew, G.H. J. Am. Chem. Soc., 1985, 107, 4265.

    Article  Google Scholar 

  181. Santa, T.; Miyata, N.; Hirobe, M. Chem. Pharm. Bull., 1984, 32, 1252. (b) Dicken, C.M.; Lu, F.-L.; Nee, M.W.; Bruice, T.C. J. Am. Chem. Soc., 1985, 107, 5776. (c) Lindsay-Smith, J.R.; Mortimer, D.N. J. Chem. Soc., Perkin Trans. II, 1986, 1743. (d) Fujimori, K.; Fujiwara, S.; Takata, T.; Oae, S. Tetrahedron Lett., 1986, 27, 581. (e) Ostovic, D.; Knobler, C.B.; Bruice, T.C. J. Am. Chem. Soc., 1987, 109, 3444.

    CAS  Google Scholar 

  182. Murahashi, S.I.; Naota, T.; Yonemura, K. J. Am. Chem. Soc., 1988, 110, 8256.

    Article  CAS  Google Scholar 

  183. Nishinaga, A.; Yamazaki, S.; Matsuura, T. Tetrahedron Lett., 1988, 29, 4115.

    CAS  Google Scholar 

  184. Minakata, S.; Ohshima, Y.; Takemiya, A.; Ryu, I.; Komatsu, M.; Ohishiro, Y. Chem. Lett., 1997, 4, 311.

    Google Scholar 

  185. Bailey, A.J.; James, B.R. J. Chem. Soc., Chem. Commun., 1996, 2343.

    Google Scholar 

  186. Cenini, S.; Porta, F.; Pizzotti, M. J. Mol. Catal., 1982, 15, 297.

    CAS  Google Scholar 

  187. Murahashi, S.I.; Naota, T.; Tali, H. J. Chem. Soc., Chem. Commun., 1985, 613.

    Google Scholar 

  188. Müller, P.; Gilabert, D.M. Tetrahedron, 1988, 44, 7171.

    Google Scholar 

  189. Porta, F.; Crotti, C.; Cenini, S. J. Mol. Catal, 1989, 50, 333.

    CAS  Google Scholar 

  190. Ananda, S.; Jagadeesha, M.B.; Puttaswamy; Gowda, N.M. Made Synth. React. Inorg. Met.-Org. Chem., 1997, 27, 1093.

    CAS  Google Scholar 

  191. Leising, V.; Ohman, J.S.; Acquaye, J.H.; Takeuchi, K.J. J. Chem. Soc., Chem. Commun., 1989, 905.

    Google Scholar 

  192. Taqui Khan, M.M.; Chatterjee, D.; Kumar, S.; Merchant, R.R.; Bhatt, K.N. J. Mol. Catal., 1991, 67, 317.

    Google Scholar 

  193. Behari, K.; Agarwal, R.K.; Gautam, M. Nat. Acad. Sci. Letters, 1986, 9, 233.

    CAS  Google Scholar 

  194. Goti, A.; Romani, M. Tetrahedron Lett., 1994, 35, 6567.

    CAS  Google Scholar 

  195. Huang, J.-S.; Leung, K.-Y.; Cheung, K.-K.; Che, C.-M. Chem. Eur. J., 2000, 6, 2971.

    CAS  Google Scholar 

  196. Huang, J.-S.; Sum, X.-R.; Leung, S.K.-Y.; Cheung, K.-K.; Che, C.-M. Chem. Eur. J., 2000, 6, 334.

    CAS  Google Scholar 

  197. Ezhova, M.; James, B.R. 11th Intern. Symp. On Homog. Catal., St Andrews, Scotland, 1998, Abstract P.241; to be published.

    Google Scholar 

  198. Morice, C.; Le Maux, P.; Simonneaux, G. Tetrahedron Lett., 1996, 37, 6701.

    Article  CAS  Google Scholar 

  199. Leung, W.-H.; Hun, T.S.M.; Hou, H.-W.; Wong, K.-Y. J. Chem. Soc., Dalton Trans., 1997, 237.

    Google Scholar 

  200. Li, Z.-Y.; Che, C.-M. Chinese J. of Chem., 1997, 15, 1.

    Google Scholar 

  201. Mansuy, D.; Battioni, P.; Mahy, J.-P. J. Am. Chem. Soc., 1982, 104, 4487. (b) Mahy, J.-P.; Battioni, P.; Mansuy, D.; Fisher, J.; Weiss, R.; Mispelter, J.; Morgenstern-Badarau, I.; Gans, P. J. Am. Chem. Soc., 1984, 106, 1699. (c) Mahy, J.-P.; Battioni, P.; Mansuy, D. J. Am. Chem. Soc., 1986, 108, 1079.

    CAS  Google Scholar 

  202. Morice, C.; Le Maux, P.; Moinet, C.; Simonneaux, G. Inorg. Chim. Acta, 1998, 273, 142.

    Article  CAS  Google Scholar 

  203. Morice, C.; Le Maux, P.; Simonneaux, G.; Toupet, L. J. Chem. Soc., Dalton Trans., 1998, 4165.

    Google Scholar 

  204. Galardon, E.; Le Maux, P.; Bondon, A.; Simonneaux, G. Tetrahedron: Asym., 1999, 10, 4203.

    Article  CAS  Google Scholar 

  205. Li, Z.-Y.; Che, C.-M. J. Inorg. Chem. (Chinese), 1997, 13, 135.

    Google Scholar 

  206. Li, Z.-Y.; Huang, J.-S.; Chan, M. C.-W.; Cheung, K.-K.; Che, C.-M. Inorg. Chem., 1997, 36, 3064.

    CAS  Google Scholar 

  207. Au, S.-M.; Fung, W.-H.; Cheng, M.-C.; Che, C.-M.; Peng, S.-M. J. Chem. Soc., Chem. Commun., 1997, 1655.

    Google Scholar 

  208. Au, S.-M.; Huang, J.-S.; Yu, W.-Y.; Fung, W.-H.; Che, C.-M. J. Am. Chem. Soc., 1999, 121, 9120.

    Article  CAS  Google Scholar 

  209. Barley, M.H.; Takeuchi, K.J.; Meyer, T.J. J. Am. Chem. Soc., 1986, 105, 5876.

    Google Scholar 

  210. Patric, D.W.; Truesdale, L.K.; Biller, S.A.; Sharpless, K.B. J. Org. Chem., 1978, 43, 2628. (b) Herranz, E.; Sharpless, K.B. J. Org. Chem., 1978, 43, 2544.

    Google Scholar 

  211. Nobis, M.; Drießen-Hölscher, B. B. Angew. Chem. Int. Ed., 2001, 40, 3983.

    CAS  Google Scholar 

  212. Bradley, D.C.; Chishlom, M.N. Acc. Chem. Res., 1976, 9, 273. (b) Chong, A.O.; Oshima, K.; Sharpless, K.B. J. Am. Chem. Soc., 1977, 99, 3420. (c) Fryzuk, M.D.; Montgomery, C.D. Coord. Chem. Rev., 1989, 95, 1.

    Article  CAS  Google Scholar 

  213. Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Che, C.-M.; J. Chem. Soc., Chem. Commun., 1999, 2377.

    Google Scholar 

  214. Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett., 2000, 2, 2233.

    CAS  Google Scholar 

  215. Au, S.-M.; Zhang, S.-B.; Fung, W.-H.; Yu, W.-Y.; Che, C.-M.; Cheung, K.-K. J. Chem. Soc., Chem. Commun., 1998, 2677.

    Google Scholar 

  216. Buchler, J.W.; Dreher, C.; Lay, K.L. Naturforsh, 1982, 37B, 1155. (b) Groves, J.T.; Takahashi, T. J. Am. Chem. Soc., 1983, 105, 2073. (c) Mansuy, D.; Mahy, J.-P.; Drureault, A.; Bedi, G.; Battioni, P. J. Chem. Soc., Chem. Commmun., 1984, 1161.

    CAS  Google Scholar 

  217. Gray, S.D.; Thorman, J.L.; Berreau, L.M.; Woo, L.K. Inorg. Chem., 1997, 36, 278. (b) Gray, S.D.; Thorman, J.L.; Adamian, V.A.; Kadish, K.M.; Woo, L.K. Inorg. Chem., 1998, 37, 1.

    Article  CAS  Google Scholar 

  218. Moubaraki, B.; Murray, K.S.; Nichols, P.J.; Thomson, S.; West, B.O. Polyhedron, 1994, 13, 485.

    Article  CAS  Google Scholar 

  219. Che, C.-M.; Huang, J.-S.; Li, Z.-Y.; Poon, C.-K. Inorg. Chim. Acta, 1991, 190, 161. (b) Smieja, J.A.; Omberg, K.M. Inorg. Chem., 1994, 33, 614.

    CAS  Google Scholar 

  220. Li, Z.; Che, C.; Poon, C. Wuhan Univ. J. of Nat. Sci., 1996, 1, 89.

    CAS  Google Scholar 

  221. Costas, M.; Rohde, J.-U.; Stubna, A.; Ho, R.Y.N.; Quaroni, L.; Münck, E.; Que, L. J. Am. Chem. Soc., 2001, 123, 12931. (b) Whittingdon, D.A.; Sazinsky, M.H.; Lippard, S.J. J. Am. Chem. Soc., 2001, 123, 1794. (c) Lee, D.; Lippard, S.J. J. Am. Chem. Soc., 2001, 123, 4611.

    CAS  Google Scholar 

  222. Karlin, K.D.; Zuberbühler, A.D. in Bioinorganic Catalysis; 2nd ed.; Revised and Expanded; (Reedijk, J.; Bouwman, E. eds.); Marcel Dekker Inc.: New York, p. 469, 1999. (b) Wilmot, C.M.; Hajdu, J.; McPherson, M.J.; Knowles, P.F.; Phillips, S.E.V. Science, 1999, 286, 1724.

    Google Scholar 

  223. Palucki, M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. J. Am. Chem. Soc., 1998, 120, 948.

    Article  CAS  Google Scholar 

  224. White, M.C.; Doyle, A.G.; Jacobsen, E.N. J. Am. Chem. Soc., 2001, 123, 7194. (b) Costas, M.; Tipton, A.; Chen, K.; Jo, D.-H.; Que, L. J. Am. Chem. Soc., 2001, 123, 6722.

    CAS  Google Scholar 

  225. Sheldon, R.A. Stud. Surface Sci. Catal, 1990, 55, 1.

    Google Scholar 

  226. Partenheimer, W. Catal. Today, 1995, 23, 69.

    Article  CAS  Google Scholar 

  227. Brothers, P.J.; Collman, J.P. Acc. Chem. Res., 1986, 19, 209.

    Article  CAS  Google Scholar 

  228. Richter-Addo, G.B.; Wheeler, R.A.; Hixson, C.A.; Chen, L.; Khan, M.A.; Ellison, M.K.; Schulz, C.E.; Scheidt, W.R. J. Am. Chem. Soc., 2001, 123, 6314. (b) Collman, J.P.; Rose, E.; Venburg, G.D. J. Chem. Soc., Chem. Commun., 1994, 11. (c) Alexander, C.S.; Rettig, S.J.; James, B.R. Organometallics, 1994, 13, 2542.

    Article  CAS  Google Scholar 

  229. Chaloner, P.A.; Esteruelas, M.A.; Joo, F.; Oro, L.A. Homogeneous Hydrogenation; Kluwer Academic Publishers: Dordrecht, 1994. (b) Hegedus, L.S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994.

    Google Scholar 

  230. Kumobayashi, H.; Miura, T.; Sayo, N.; Saito, T.; Zhang, X. Synlett., 2001, 1055. (b) Wiles, J.A.; Bergens, S.H.; Young, V.G. Can. J. Chem., 2001 79, 1019. (c) Noyori, R.; Ohkuma, T. Angew. Chem. Int. Ed, 2001, 40, 40. (d) Noyori, R. Acta Chem. Scand,. 1996, 50, 380.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada

    Maria B. Ezhova & Brian R. James

Authors
  1. Maria B. Ezhova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Brian R. James
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Chemical Research Center, Hungarian Academy of Sciences, Budapest

    László I. Simándi

Rights and permissions

Reprints and permissions

Copyright information

© 2003 Kluwer Academic Publishers

About this chapter

Cite this chapter

Ezhova, M.B., James, B.R. (2003). Catalytic oxidations using ruthenium porphyrins. In: Simándi, L.I. (eds) Advances in Catalytic Activation of Dioxygen by Metal Complexes. Catalysis by Metal Complexes, vol 26. Springer, Boston, MA. https://doi.org/10.1007/0-306-47816-1_1

Download citation

  • DOI: https://doi.org/10.1007/0-306-47816-1_1

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4020-1074-3

  • Online ISBN: 978-0-306-47816-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation