Skip to main content
Log in

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

  • Published:
Catalysis Letters Aims and scope Submit manuscript

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.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. J. F. Larrow and E. N. Jacobsen, Topics Organomet. Chem. 6 (2004) 123 and references therein.

    Google Scholar 

  2. T. Katsuki, Coord. Chem. Rev. 140 (1995) 189.

    Google Scholar 

  3. S. B. Ogunwumi and T. Bein, Chem. Commun. (1997) 901.

  4. J. M. Fraile, J. I. Garcia, J. Massam and J. A. Mayoral, J. Mol. Catal. A: Chem. 136 (1998) 47.

    Google Scholar 

  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. L. Frunnza, H. Kosslick, H. Landmesser, E. Ho ¨ft and R. Fricke, J. Mol. Catal. A:Chem. 123 (1997) 179.

    Google Scholar 

  7. G.-J. Kim and J.-H. Shin, Tetrahedron Lett. 40 (1999) 6827.

    Google Scholar 

  8. B. D. De, B. B. Lohray and P. K. Dhal, Tetrahedron Lett. 34 (1993) 2371.

    Google Scholar 

  9. F. Minutolo, D. Pini, A. Petri and P. Salvadori, Tetrahedron: Asymmetry 7 (1996) 2293.

    Google Scholar 

  10. L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, Chem. Commun. (1998) 2561.

  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. T. S. Reger and K. D. Janda, J. Am. Chem. Soc. 122 (2000) 6929.

    Google Scholar 

  13. C. E. Song, E. J. Roh, B. M. Yu, D. Y. Chi, S. C. Kim and K.-J. Lee, Chem. Commun. (2000) 615.

  14. K. Smith and C.-H. Liu, Chem. Commun. (2002) 886.

  15. R. Broinbauer and E. N. Jacobsen, Angew. Chem. Int. Ed. 39 (2000) 3604.

    Google Scholar 

  16. C. Pozzi, M. Cavazzini, F. Cinato, F. Montanan and S. Quici, Eur. J. Org. Chem. (1999) 1947.

  17. T. Welton, Chem. Rev. 99 (1999) 2071.

    Google Scholar 

  18. P. Wasserscheid and W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772.

    Google Scholar 

  19. R. Sheldon, Chem. Commun. (2001) 2399.

  20. C. M. Gordon, Applied Catal. A: Chem. 222 (2001) 101.

    Google Scholar 

  21. D. Zhao, M. Wu, Y. Kou and E. Z. Min, Catal. Today 74 (2002) 157.

    Google Scholar 

  22. H. Oliver-Bourbigou and L. Magna, J. Mol. Catal. A: Chem. 182 –183 (2002) 419.

    Google Scholar 

  23. P. Wasserscheid and T. Welton in: Ionic Liquids in Synthesis (Wiley-VCH, Weinheim, 2003).

    Google Scholar 

  24. S. A. Rorsyth, J. M. Pringle and D. R. MacFarlane, Aust. J. Chem. 57 (2004) 113.

    Google Scholar 

  25. N. Brausch, A. Metlen and P. Wasserscheid, Chem. Commun. (2004) 1552.

  26. C. E. Song, Chem. Commun. (2004) 1033.

  27. C. E. Song and E. J. Roh, Chem. Commun. (2000) 837.

  28. K. Smith, S. Lock, G. A. El-Hiti, M. Wada and N. Miyoshi, Org. Biomol. Chem. 2 (2004) 935.

    Google Scholar 

  29. K. Smith, S. D. Roberts and G. A. El-Hiti, Org. Biomol. Chem. 1 (2003) 1552.

    Google Scholar 

  30. K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 1560.

    Google Scholar 

  31. K. Smith, G. A. El-Hiti, A. Jayne and M. Butters, Org. Biomol. Chem. 1 (2003) 2321.

    Google Scholar 

  32. K. Smith, S. Almeer, S. J. Black and C. Peters, J. Mat. Chem. 12 (2002) 3285.

    Google Scholar 

  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. K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Synthesis (2004) in press.

  35. K. Smith, G. A. El-Hiti and M. F. Abdel-Megeed, Russ. J. Org. Chem. 39 (2003) 430.

    Google Scholar 

  36. K. Smith, G. A. El-Hiti and S. A. Mahgoub, Synthesis (2003) 2345.

  37. K. Smith, G. A. El-Hiti and A. C. Hawes, Synthesis (2003) 2047.

  38. H. Sasaki, R. Irie, T. Hamada, K. Suzuki and T. Katsuki, Tetrahedron 50 (1994) 11827.

    Google Scholar 

  39. A. G. Avent, P. A. Chaloner, M. P. Day, K. R. Seddon and T. Welton, J. Chem. Soc., Dalton Trans. (1994) 3405.

  40. J. D. Holbery and K. R. Seddon, J. Chem. Soc., Dalton Trans. (1999) 2133.

  41. J. Fuller, R. T. Carlin, H. C. De Long and D. Haworth, J. Chem. Soc., Chem. Commun. (1994) 299.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Smith, K., Liu, S. & El-Hiti, G.A. Use of Ionic Liquids as Solvents for Epoxidation Reactions Catalysed by a Chiral Katsuki-Type Salen Complex: Enhanced Reactivity and Recovery of Catalyst. Catalysis Letters 98, 95–101 (2004). https://doi.org/10.1007/s10562-004-7921-9

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-004-7921-9

Navigation