Skip to main content
Log in

Cobalt(II) schiff base functionalized mesoporous silica as an efficient and recyclable chemoselective acetalization catalyst

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Cobalt(II) Schiff base functionalized mesoporous silica was synthesized from covalent attachment via the introduction of Co(OAc)2 to salicylaldimine functionalized mesoporous silica. The catalyst proved to be chemoselective one for the acetalization of aldehydes to the corresponding acetals in alcohol. The immobilized catalyst can be easily recovered and reused for at least ten reaction cycles without significant loss of its catalytic activity.

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. S. Tamagaki, R.J. Card, D.C. Neckers, J. Am. Chem. Soc. 100 (1978) 6635.

    CAS  Google Scholar 

  2. A.P. Wight, M.E. Davis, Chem. Rev. 102 (2002) 3569.

    Google Scholar 

  3. A. Taguchi, F. Schuth, Micropor. Mesopor. Mater. 77 (2005) 1.

    CAS  Google Scholar 

  4. A. Corma, H. Garcia, Chem. Rev. 102 (2002) 3837.

    CAS  Google Scholar 

  5. D.E. DeVos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102 (2002) 3615.

    CAS  Google Scholar 

  6. L. Yin, J. Liebscher, Chem. Rev. 107 (2007) 133.

    CAS  Google Scholar 

  7. N.E. Leadbeater, M. Marco, Chem. Rev. 102 (2002) 3217.

    CAS  Google Scholar 

  8. L. Canali, D.C. Sherrington, Chem. Rev. 81 (1981) 557.

    Google Scholar 

  9. Q.-H. Fan, Y.-M. Li, A.S.C. Chan, Chem. Rev. 102 (2002) 3385.

    CAS  Google Scholar 

  10. C.E. Song, S. Lee, Chem. Rev. 102 (2002) 3495.

    CAS  Google Scholar 

  11. P. Sutra, D. Brunel, Chem. Commun. (1996) 2485.

    Google Scholar 

  12. R.J.P. Corriu, E. Lancelle-Beltran, A. Mehdi, C. Reye, S. Brandes, R. Guilard, Chem. Mater. 15 (2003) 3152.

    CAS  Google Scholar 

  13. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 3th ed., Wiley, New York, 1999.

    Book  Google Scholar 

  14. P.J. Kocienski, Protecting Groups, Thieme, New York, 1994.

    Google Scholar 

  15. H.J.E. Loewnthal, in: J.F.W. McOmie (Ed.), Protective Groups in Organic Chemistry, Plenum Press, London, 1973.

    Google Scholar 

  16. J.R. Hanson, Protecting Groups in Organic Synthesis, 1st ed., Blackwell Science, Inc: Malden, Mass., 1999.

    Google Scholar 

  17. J.N. Shepherd, D.C. Myles, Org. Lett. 5 (2003) 1027.

    CAS  Google Scholar 

  18. J.K. Whitesell, Chem. Rev. 89 (1989) 1581.

  19. D. Seebach, R. Imwinkelried, T. Weber, in: R. Schffold (Ed.), Modern Synthetic Methods, Vol. 4, Springer-Verlag, Berlin, 1986, pp. 125–259.

    Chapter  Google Scholar 

  20. J. Otera, T. Mizutani, H. Nazaki, Organometallics 8 (1989) 2063.

    CAS  Google Scholar 

  21. B. Karimi, B. Golshani, Synthesis (2002) 784.

    Google Scholar 

  22. S. Vetrivel, A. Pandurangan, J. Mol. Catal. A 217 (2004) 165.

    CAS  Google Scholar 

  23. C.T. Chen, S.S. Weng, J.Q. Kao, C.C. Lin, M.D. Jan, Org. Lett. 7 (2005) 3343.

    CAS  Google Scholar 

  24. B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett (1999) 1456.

    Google Scholar 

  25. A.J.F. Meskens, Synthesis (1981) 501.

    Google Scholar 

  26. R. Gopinath, S.J. Haque, B.K. Patel, J. Org. Chem. 67 (2002) 5842.

    CAS  Google Scholar 

  27. B. Perio, M.J. Dozians, P. Jacquault, J. Hamelin, Tetrahedron Lett. 38 (1997) 7867.

    CAS  Google Scholar 

  28. S.H. Lee, J.H. Lee, C.M. Yoon, Tetrahedron Lett. 43 (2002) 2699.

    CAS  Google Scholar 

  29. J. Tateiwa, H. Horiuchi, S. Uemura, J. Org. Chem. 60 (1995) 4039.

    CAS  Google Scholar 

  30. S. Velusamy, T. Punniyamurthy, Tetrahedron Lett. 45 (2004) 4917.

    CAS  Google Scholar 

  31. B.M. Smith, A.E. Graham, Tetrahedron Lett. 47 (2006) 9317.

    CAS  Google Scholar 

  32. B.T. Gregg, K.C. Golden, J.F. Quinn, Tetrahedron 64 (2008) 3287.

    CAS  Google Scholar 

  33. N.M. Leonard, M.C. Oswald, D.A. Freiberg, B.A. Nattier, R.C. Smith, R.S. Mohan, J. Org. Chem. 67 (2002) 5202.

    CAS  Google Scholar 

  34. J. Otera, N. Dan-Oh, H. Nozaki, Tetrahehron 48 (1992) 1449.

    CAS  Google Scholar 

  35. H. Firouzabadi, N. Iranpoor, B. Karimi, Synth. Commun. 29 (1999) 2255.

    CAS  Google Scholar 

  36. B. Karimi, M. Ghoreishi-Nezhad, J. Mol. Catal. A 277 (2007) 262.

    CAS  Google Scholar 

  37. I. Rodriguez, M.J. Climent, S. Iborra, V. Fornes, A. Corma, J. Catal. 192 (2000) 441.

    CAS  Google Scholar 

  38. M.V. Joshi, C.S. Narasimhan, J. Catal. 128 (1991) 63.

    CAS  Google Scholar 

  39. M.W.C. Robinson, A.E. Graham, Tetrahedron Lett. 48 (2007) 4727.

    CAS  Google Scholar 

  40. W.M. Van Rhijn, D.E. DeVor, B.F. Sels, W.D. Bossaert, P.A. Jacobs, Chem. Commun. (1998) 317.

    Google Scholar 

  41. D. Margolese, J.A. Melero, S.C. Christiansen, B.F. Chmelka, G.D. Stucky, Chem. Mater. 12 (2000) 2448.

    CAS  Google Scholar 

  42. K. Wilson, A. Renson, J.H. Clark, Pure Appl. Chem. 72 (2000) 1313.

    CAS  Google Scholar 

  43. M.H. Lim, C.F. Blanford, A. Stein, Chem. Mater. 10 (1998) 467.

    CAS  Google Scholar 

  44. Q. Bao, K. Qiao, D. Tomida, C. Yokoyama, Catal. Commun. 10 (2009) 1625.

    CAS  Google Scholar 

  45. C. Huo, T.H. Chan, Adv. Synth. Catal. 351 (2009) 1933.

    CAS  Google Scholar 

  46. F. Rajabi, J.H. Clark, B. Karimi, D.J. Macquarrie, Org. Biomol. Chem. 3 (2005) 725.

    CAS  Google Scholar 

  47. F. Rajabi, B. Karimi, J. Mol. Catal. A: Chem. 232 (2005) 95.

    CAS  Google Scholar 

  48. I.C. Chisem, J. Rafelt, M.T. Shieh, J. Chisem, J.H. Clark, R. Jachuck, D. Macquarrie, C. Ramshaw, K. Scott, Chem. Commun. (1998) 1949.

    Google Scholar 

  49. F. Rajabi, Tetrahedron Lett. 50 (2009) 395.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rajabi, F. Cobalt(II) schiff base functionalized mesoporous silica as an efficient and recyclable chemoselective acetalization catalyst. JICS 7, 695–701 (2010). https://doi.org/10.1007/BF03246059

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03246059

Keywords

Navigation