Catalysis Letters

, Volume 98, Issue 2–3, pp 95–101 | Cite as

Use of Ionic Liquids as Solvents for Epoxidation Reactions Catalysed by a Chiral Katsuki-Type Salen Complex: Enhanced Reactivity and Recovery of Catalyst

  • Keith Smith
  • Shifang Liu
  • Gamal A. El-Hiti
Article

Abstract

The Katsuki-type catalyst 2 has been recycled several times following its use in a model epoxidation reaction of 1,2-dihydronaphthalene in an ionic liquid, 3a or 3b. The enantioselectivity was comparable to that in dichloromethane, but recovery of the catalyst was easier, activity was higher, and activity and enantioselectivity were retained in recovered ionic liquid fractions to a much greater extent than those for the Jacobsen-type catalyst 1.

Ionic liquids Katsuki-type chiral catalyst Two-phase systems Epoxidation 2-dihydronaphthalene. 

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References

  1. [1]
    J. F. Larrow and E. N. Jacobsen, Topics Organomet. Chem. 6 (2004) 123 and references therein.Google Scholar
  2. [2]
    T. Katsuki, Coord. Chem. Rev. 140 (1995) 189.Google Scholar
  3. [3]
    S. B. Ogunwumi and T. Bein, Chem. Commun. (1997) 901.Google Scholar
  4. [4]
    J. M. Fraile, J. I. Garcia, J. Massam and J. A. Mayoral, J. Mol. Catal. A: Chem. 136 (1998) 47.Google Scholar
  5. [5]
    K. B. M. Janssen, I. Laquiere, W. Dehaen, R. F. Parton, I. F. J. Vankelecom and P. A. Jacobs, Tetrahedron:Asymmetry 8 (1997) 3481.Google Scholar
  6. [6]
    L. Frunnza, H. Kosslick, H. Landmesser, E. Ho ¨ft and R. Fricke, J. Mol. Catal. A:Chem. 123 (1997) 179.Google Scholar
  7. [7]
    G.-J. Kim and J.-H. Shin, Tetrahedron Lett. 40 (1999) 6827.Google Scholar
  8. [8]
    B. D. De, B. B. Lohray and P. K. Dhal, Tetrahedron Lett. 34 (1993) 2371.Google Scholar
  9. [9]
    F. Minutolo, D. Pini, A. Petri and P. Salvadori, Tetrahedron: Asymmetry 7 (1996) 2293.Google Scholar
  10. [10]
    L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, Chem. Commun. (1998) 2561.Google Scholar
  11. [11]
    L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, J. Chem. Soc., Perkin Trans. 1 (2000) 2055.Google Scholar
  12. [12]
    T. S. Reger and K. D. Janda, J. Am. Chem. Soc. 122 (2000) 6929.Google Scholar
  13. [13]
    C. E. Song, E. J. Roh, B. M. Yu, D. Y. Chi, S. C. Kim and K.-J. Lee, Chem. Commun. (2000) 615.Google Scholar
  14. [14]
    K. Smith and C.-H. Liu, Chem. Commun. (2002) 886.Google Scholar
  15. [15]
    R. Broinbauer and E. N. Jacobsen, Angew. Chem. Int. Ed. 39 (2000) 3604.Google Scholar
  16. [16]
    C. Pozzi, M. Cavazzini, F. Cinato, F. Montanan and S. Quici, Eur. J. Org. Chem. (1999) 1947.Google Scholar
  17. [17]
    T. Welton, Chem. Rev. 99 (1999) 2071.Google Scholar
  18. [18]
    P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772.Google Scholar
  19. [19]
    R. Sheldon, Chem. Commun. (2001) 2399.Google Scholar
  20. [20]
    C. M. Gordon, Applied Catal. A: Chem. 222 (2001) 101.Google Scholar
  21. [21]
    D. Zhao, M. Wu, Y. Kou and E. Z. Min, Catal. Today 74 (2002) 157.Google Scholar
  22. [22]
    H. Oliver-Bourbigou and L. Magna, J. Mol. Catal. A: Chem. 182 –183 (2002) 419.Google Scholar
  23. [23]
    P. Wasserscheid and T. Welton in: Ionic Liquids in Synthesis (Wiley-VCH, Weinheim, 2003).Google Scholar
  24. [24]
    S. A. Rorsyth, J. M. Pringle and D. R. MacFarlane, Aust. J. Chem. 57 (2004) 113.Google Scholar
  25. [25]
    N. Brausch, A. Metlen and P. Wasserscheid, Chem. Commun. (2004) 1552.Google Scholar
  26. [26]
    C. E. Song, Chem. Commun. (2004) 1033.Google Scholar
  27. [27]
    C. E. Song and E. J. Roh, Chem. Commun. (2000) 837.Google Scholar
  28. [28]
    K. Smith, S. Lock, G. A. El-Hiti, M. Wada and N. Miyoshi, Org. Biomol. Chem. 2 (2004) 935.Google Scholar
  29. [29]
    K. Smith, S. D. Roberts and G. A. El-Hiti, Org. Biomol. Chem. 1 (2003) 1552.Google Scholar
  30. [30]
    K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 1560.Google Scholar
  31. [31]
    K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 2321.Google Scholar
  32. [32]
    K. Smith, S. Almeer, S. J. Black and C. Peters, J. Mat. Chem. 12 (2002) 3285.Google Scholar
  33. [33]
    K. Smith, G. A. El-Hiti, M. E. W. Hammond, D. Bahzad, Z. Li and C. Siquet, J. Chem. Soc., Perkin Trans. 1 (2000) 2745.Google Scholar
  34. [34]
    K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Synthesis (2004) in press.Google Scholar
  35. [35]
    K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Russ. J. Org. Chem. 39 (2003) 430.Google Scholar
  36. [36]
    K. Smith, G. A. El-Hiti and S. A. Mahgoub, Synthesis (2003) 2345.Google Scholar
  37. [37]
    K. Smith, G. A. El-Hiti and A. C. Hawes, Synthesis (2003) 2047.Google Scholar
  38. [38]
    H. Sasaki, R. Irie, T. Hamada, K. Suzuki and T. Katsuki, Tetrahedron 50 (1994) 11827.Google Scholar
  39. [39]
    A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans. (1994) 3405.Google Scholar
  40. [40]
    J. D. Holbery and K. R. Seddon, J. Chem. Soc., Dalton Trans. (1999) 2133.Google Scholar
  41. [41]
    J. Fuller, R. T. Carlin, H. C. De Long and D. Haworth, J. Chem. Soc., Chem. Commun. (1994) 299.Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • Keith Smith
    • 1
  • Shifang Liu
    • 1
  • Gamal A. El-Hiti
    • 1
  1. 1.Department of ChemistryCentre for Clean Chemistry, University of Wales SwanseaSwanseaUK

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