Organometallic Oxidation Catalysis pp 39-77

Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 22)

Organorhenium and Organomolybdenum Oxides as Heterogenised Catalysts

  • Christelle Freund
  • Wolfgang Herrmann
  • Fritz E. Kühn
Chapter

Abstract

A variety of organomolybdenum and organorhenium complexes, most prominently methyltrioxorhenium(VII) (MTO), are applicable as efficient and selective oxidising agents in the presence of organic hydroperoxides (molybdenum complexes) or hydrogen peroxide (rhenium complexes). Besides strictly homogeneous oxidation catalysis, there is increasing interest in immobilizing homogeneous catalysts, both on carrier materials and in ionic liquids. Several methods that differ mainly in the anchoring mode and the nature of the supporting material have been described, and the resulting materials were applied to oxidation catalysis. Chiral oxidation catalysis with the compounds mentioned in the title is still in its infancy, but initial results point towards a promising future. The supported catalysts combine properties of homogeneous catalysts (reactivity, control and selectivity) and heterogeneous catalysts (enhanced stability and reusability). Homogeneous catalysts have a clearly defined composition, and mechanistic examinations are usually less problematic than with bulk (heterogeneous) catalysts, where the active sites are less clearly defined. It is also more straightforward to modify homogeneous catalysts by fine-tuning their ligand environments.

Organomolybdenum complexes Organorhenium complexes Oxidation catalysis Heterogenisation 

Abbreviations

acac

acetylacetonate

bpy

2,2′-bipyridyl

Cp

cyclopentadiene

dppa

bis(diphenylphosphino)amine

Et

ethyl

EXAFS

extended X-ray absorption fine structure

IR

infrared

MCM

mobile crystalline material

Me

methyl

MTO

methyltrioxorhenium

NMR

nuclear magnetic resonance

PBI

polybenzimidazole

PEO

polyethylene oxide

Ph

phenyl

PPO

polypropylene oxide

PS

polystyrene

PSHPAMP

polystyrene–divinylbenzene resin carrying an N-(2-hydroxypropyl)- 2-aminomethylpyridine ligand

PVP

poly(4-vinylpyridine)

PVPN

poly(4-vinylpyridine-N-oxide)

RT

room temperature

RTIL

room temperature ionic liquid

TBHP

tert-butyl hydroperoxide

UHP

urea hydroperoxide

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kumar SB, Chaudhury M (1991) J Chem Soc Dalton Trans p 2169 Google Scholar
  2. 2.
    Palanca P, Picher T, Sanz V, Gomez-Romero P, Llopis E, Domenech A, Cervilla A (1990) J Chem Soc Chem Commun p 531 Google Scholar
  3. 3.
    Wilshire JP, Leon L, Bosserman P, Sawyer DT (1979) J Am Chem Soc 101:3379 CrossRefGoogle Scholar
  4. 4.
    Berg JM, Holm RH (1985) J Am Chem Soc 107:925 CrossRefGoogle Scholar
  5. 5.
    Caradonna JP, Harlan EW, Holm RH (1986) J Am Chem Soc 108:7856 CrossRefGoogle Scholar
  6. 6.
    Fehrer FJ, Rahimian K, Budzichowski TA, Ziller JW (1995) Organometallics 14:3920 CrossRefGoogle Scholar
  7. 7.
    Clarke R, Gahagan M, Mackie RK, Foster DF, Cole-Hamilton DJ, Nicol M, Montford AW (1995) J Chem Soc Dalton Trans p 1221 Google Scholar
  8. 8.
    Backhouse JR, Lowe HM, Sinn E, Suzuki S, Woodward S (1995) J Chem Soc Dalton Trans p 3329 Google Scholar
  9. 9.
    Kollar J (Halcon International Inc.) (1967) US Patent 3 350 422 Google Scholar
  10. 10.
    Kollar J (Halcon International Inc.) (1967) US Patent 3 351 635 Google Scholar
  11. 11.
    Sheng MN, Zajaczek GJ (ARCO) (1968) UK Patent: GB 1 136 923 Google Scholar
  12. 12.
    Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck S (1992) Nature 359:710 CrossRefGoogle Scholar
  13. 13.
    Beck S, Vartuli JC, Roth WJ, Leonowicz ME, Kresge CT, Schmitt KD, Chu CT-W, Olson DH, Sheppard EW, McCullen SB, Higgins JB, Schlenker JL (1992) J Am Chem Soc 114:10834 CrossRefGoogle Scholar
  14. 14.
    Alfredsson V, Anderson M (1996) Chem Mater 8:1141 CrossRefGoogle Scholar
  15. 15.
    Ferreira P, Gonçalves IS, Kühn FE, Lopez AD, Martins MA, Pillinger M, Pina A, Rocha J, Romão CC, Santos AM, Santos TM, Valente AA (2000) Eur J Inorg Chem p 2263 Google Scholar
  16. 16.
    Sakthivel A, Zhao J, Kühn FE (2005) Catal Lett 102:115 CrossRefGoogle Scholar
  17. 17.
    Sakthivel A, Zhao J, Hanzlik M, Kühn FE (2004) Dalton Trans p 3338 Google Scholar
  18. 18.
    Corma A, Fuerte A, Iglesias M, Sanchez F (1996) J Mol Catal A–Chem 107:225 CrossRefGoogle Scholar
  19. 19.
    Sakthivel A, Zhao J, Hanzlik M, Chiang AST, Herrmann WA, Kühn FE (2005) Adv Synth Catal 347:473 CrossRefGoogle Scholar
  20. 20.
    Abrantes M, Gago S, Valente AA, Pillinger M, Gonçalves IS, Santos TM, Rocha J, Romão CC (2004) Eur J Inorg Chem 4914 Google Scholar
  21. 21.
    Sakthivel A, Abrantes M, Chiang AST, Kühn FE (2006) J Organomet Chem 691:1007 CrossRefGoogle Scholar
  22. 22.
    Jia M, Thiel WR (2002) Chem Commun p 2392 Google Scholar
  23. 23.
    Jia M, Seifert A, Thiel WR (2003) Chem Mater 15:2174 CrossRefGoogle Scholar
  24. 24.
    Nunes CD, Valente AA, Pillinger M, Fernandes AC, Romão CC, Rocha J, Gonçalves IS (2002) J Mater Chem 12:1735 CrossRefGoogle Scholar
  25. 25.
    Sakthivel A, Zhao J, Raudaschl-Sieber G, Kühn FE (2005) J Organomet Chem 690:5105 CrossRefGoogle Scholar
  26. 26.
    Gonçalves IS, Santos AM, Romão CC, Lopez AD, Rodriguez-Borges JE, Pillinger M, Ferreira P, Rocha J, Kühn FE (2001) J Organomet Chem 626:1 CrossRefGoogle Scholar
  27. 27.
    Sakthivel A, Zhao J, Raudaschl-Sieber G, Hanzlik M, Chiang AST, Kühn FE (2005) Appl Cat A 281:267 CrossRefGoogle Scholar
  28. 28.
    Jia M, Seifert A, Berger M, Giegengack H, Schulze S, Thiel WR (2004) Chem Mater 16:877 CrossRefGoogle Scholar
  29. 29.
    Jia M, Seifert A, Thiel WR (2004) J Catal 221:319 CrossRefGoogle Scholar
  30. 30.
    Sherrington DC, Simpson S (1991) J Catal 131:115 CrossRefGoogle Scholar
  31. 31.
    Sherrington DC, Simpson S (1993) React Polym 19:13 CrossRefGoogle Scholar
  32. 32.
    Miller MM, Sherrington DC (1994) J Chem Soc Perkin Trans 2:2091 Google Scholar
  33. 33.
    Miller MM, Sherrington DC (1995) J Catal 152:368 CrossRefGoogle Scholar
  34. 34.
    Ahn JH, Sherrington DC (1996) J Chem Soc Chem Commun p 643 Google Scholar
  35. 35.
    Valente AA, Petrovski Z, Branco LC, Afonso CAM, Pillinger M, Lopez AD, Romão CC, Nunes CD, Gonçalves IS (2004) J Mol Catal A–Chem 218:5 CrossRefGoogle Scholar
  36. 36.
    Kühn FE, Zhao J, Abrantes M, Sun W, Afonso CAM, Branco LC, Gonçalves IS, Pillinger M, Romão CC (2005) Tetrahedron Lett 46:47 CrossRefGoogle Scholar
  37. 37.
    Kühn FE, Lopes AD, Santos AM, Herdtweck E, Haider JJ, Romão CC, Santos AG (2000) J Mol Catal A–Chem 151:147 CrossRefGoogle Scholar
  38. 38.
    Sakthivel A, Zhao J, Kühn FE (2005) Micropor Mesopor Mater 86:341 CrossRefGoogle Scholar
  39. 39.
    Abrantes M, Santos AM, Mink J, Kühn FE, Romão CC (2003) Organometallics 22:2112 CrossRefGoogle Scholar
  40. 40.
    Gago S, Pillinger M, Valente AA, Santos TM, Rocha J, Gonçalves IS (2004) Inorg Chem 43:5422 CrossRefGoogle Scholar
  41. 41.
    Zhao J, Sakthivel A, Santos AM, Kühn FE (2005) Inorg Chim Acta 358:4201 CrossRefGoogle Scholar
  42. 42.
    Sakthivel A, Zhao J, Kühn FE (2005) Bull Catal Soc India 4:79 Google Scholar
  43. 43.
    Zhao XS, Lu GQ (1998) J Phys Chem B 102:1556 CrossRefGoogle Scholar
  44. 44.
    Tatsumi T, Koyano A, Tanaka Y, Nakata S (1998) Stud Surf Sci Catal 117:143 CrossRefGoogle Scholar
  45. 45.
    Miller MM, Sherrington DC (1994) J Chem Soc Chem Commun 55 Google Scholar
  46. 46.
    Miller MM, Sherrington DC (1995) J Catal 152:377 CrossRefGoogle Scholar
  47. 47.
    Leinonen S, Sherrington DC, Sneddon A, McLoughlin D, Corker J, Canevali C, Morazzoni F, Reedjik J, Spratt SPD (1999) J Catal 183:251 CrossRefGoogle Scholar
  48. 48.
    Song CE, Roh EH (2000) Chem Commun p 837 Google Scholar
  49. 49.
    Li Z, Xia C-G (2003) Tetrahedron Lett 44:2069 CrossRefGoogle Scholar
  50. 50.
    Li Z, Xia C-G, Ji M (2003) Appl Cat A–Gen 252:17 CrossRefGoogle Scholar
  51. 51.
    Kühn FE, Santos AM, Herrmann WA (2005) Dalton Trans p 2483 Google Scholar
  52. 52.
    Buffon R, Leconte M, Basset J-M, Touroude R, Herrmann WA (1992) J Mol Catal A–Chem 72:139 CrossRefGoogle Scholar
  53. 53.
    Buffon R, Choplin A, Leconte M, Basset J-M, Touroude R, Herrmann WA (1992) J Mol Catal A–Chem 72:L7 CrossRefGoogle Scholar
  54. 54.
    Buffon R, Auroux A, Lefebvre F, Leconte M, Choplin A, Basset J-M, Herrmann WA (1992) J Mol Catal A–Chem 76:287 CrossRefGoogle Scholar
  55. 55.
    Zhu Z, Espenson JH (1997) J Mol Catal A–Chem 121:139 CrossRefGoogle Scholar
  56. 56.
    Bouh AO, Espenson JH (2003) J Mol Catal A–Chem 200:43 CrossRefGoogle Scholar
  57. 57.
    Li M, Espenson JH (2004) J Mol Catal A–Chem 208:123 CrossRefGoogle Scholar
  58. 58.
    Herrmann WA, Kuchler JG, Felixberger JK, Herdtweck E, Wagner W (1988) Anal Chem 27:394 Google Scholar
  59. 59.
    Neumann R, Wang T-J (1997) J Chem Soc Chem Commun p 1915 Google Scholar
  60. 60.
    Dallmann K, Buffon R (2000) Catal Commun 1:9 CrossRefGoogle Scholar
  61. 61.
    Nunes CD, Pillinger M, Valente AA, Gonçalves IS, Rocha J, Ferreira P, Kühn FE (2002) Eur J Inorg Chem p 1100 Google Scholar
  62. 62.
    Sakthivel A, Raudaschl-Sieber G, Kühn FE (2006) Dalton Trans p 468 Google Scholar
  63. 63.
    Wang T-J, Li D-C, Bai J-H, Huang M-Y, Jiang Y-Y (1998) J Macromol Sci Pure 35:531 CrossRefGoogle Scholar
  64. 64.
    Adam W, Saha-Möller CR, Weichold O (2000) J Org Chem 65:2897 CrossRefGoogle Scholar
  65. 65.
    Adam W, Mitchell CM (1996) Angew Chem Int Ed 35:533 CrossRefGoogle Scholar
  66. 66.
    Adam W, Mitchell CM, Saha-Möller CR, Weichold O (1999) J Am Chem Soc 121:2097 CrossRefGoogle Scholar
  67. 67.
    Saladino R, Carlucci P, Danti MC, Crestini C, Mincione E (2000) Tetrahedron 56:10031 CrossRefGoogle Scholar
  68. 68.
    Sica D, Musumeci D, Zollo F, de Marino S (2001) Eur J Org Chem 19:3731 CrossRefGoogle Scholar
  69. 69.
    Sica D, Musumeci D, Zollo F, de Marino S (2001) J Chem Soc Perkin Trans 1:1889 CrossRefGoogle Scholar
  70. 70.
    Herrmann WA, Wagner W, Flessner UN, Volkhardt U, Komber H (1991) Angew Chem Int Ed 30:1636 CrossRefGoogle Scholar
  71. 71.
    Herrmann WA, Fritz-Meyer-Weg DM, Wagner W, Kuchler JG, Weichselbaumer G, Fischer RW (Hoechst AG) (1992) US Patent 155 247 Google Scholar
  72. 72.
    Saladino R, Neri V, Pellicia AR, Caminiti R, Sadun C (2002) J Org Chem 67:1323 CrossRefGoogle Scholar
  73. 73.
    Saladino R, Neri V, Pelliccia AR, Mincione E (2003) Tetrahedron 59:7403 CrossRefGoogle Scholar
  74. 74.
    Bernini R, Mincione E, Cortese M, Saladino R, Gualandi G, Belfiore MC (2003) Tetrahedron Lett 44:4823 CrossRefGoogle Scholar
  75. 75.
    Bianchini G, Crucianelli M, De Angelis F, Neri V, Saladino R (2004) Tetrahedron Lett 45:2351 CrossRefGoogle Scholar
  76. 76.
    Bianchini G, Crucianelli M, De Angelis F, Neri V, Saladino R (2005) Tetrahedron Lett 46:2427 CrossRefGoogle Scholar
  77. 77.
    Owens GS, Abu-Omar MM (2000) Chem Commun p 1165 Google Scholar
  78. 78.
    Bernini R, Coratti A, Fabrizi G, Goggiamani A (2003) Tetrahedron Lett 44:8991 CrossRefGoogle Scholar
  79. 79.
    Rost AMJ, Schneider H, Zoller JP, Herrmann WA, Kühn FE (2005) J Organomet Chem 690:4712 CrossRefGoogle Scholar
  80. 80.
    Bein T, Huber C, Moller K, Wu CG, Xu L (1997) Chem Mater 9:2252 CrossRefGoogle Scholar
  81. 81.
    Owens GS, Abu-Omar MM (2002) J Mol Catal A–Chem 187:215 CrossRefGoogle Scholar
  82. 82.
    Owens GS, Durazo A, Abu-Omar MM (2002) Chem Eur J 8:3053 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  • Christelle Freund
    • 1
  • Wolfgang Herrmann
    • 1
  • Fritz E. Kühn
    • 1
    • 2
  1. 1.Lehrstuhl für Anorganische Chemie der Technischen Universität MünchenGarchingGermany
  2. 2.Departamento de Química, Instituto Tecnológico e Nuclear (ITN)SacavémPortugal

Personalised recommendations