Skip to main content
Log in

Palladium nanoparticles supported on an organosuperbase denderon-modified mesoporous SBA-15 as a heterogeneous catalyst in Heck coupling reaction

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

An efficient synthetic method for successful synthesis of basic amine denderon on SBA-15 and related Pd(II) complex as a novel catalyst has been developed. This modified mesoporous material was characterized by various techniques such as TEM, XRD, atomic absorption spectroscopy, N2 adsorption–desorption, and FT-IR. The prepared novel heterogeneous catalyst was evaluated in Heck coupling reaction. The very stable hybrid material catalyst was easily recovered, showed negligible Pd leaching, and retained good activity for at least ten successive runs without any additional activation. The catalytic activities of the prepared catalysts were investigated by employing aerobic oxidation of alcohols and Heck coupling as model reactions. The yields of the products were in the range from 75 to 92 %. The catalyst can be readily recovered and reused at least five consecutive cycles without significant leaching and loss its catalytic activity.

Graphical abstract

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.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Z. Gao, Y. Feng, F. Cui, Z. Hua, J. Zhou, Y. Zhu, J. Shi, J. Mol. Catal. A Chem. 336, 51 (2011)

    Article  CAS  Google Scholar 

  2. V. Polshettiwar, P. Hesemann, J.E.J. Moreau, Tetrahedron 63, 6784 (2007)

    Article  CAS  Google Scholar 

  3. K. Qiao, R. Sugimura, Q. Bao, D. Tomida, C. Yokoyama, Catal. Commun. 9, 2470 (2008)

    Article  CAS  Google Scholar 

  4. J.Z. Jiang, C.J. Cai, Colloid Interface Sci. 299, 938 (2006)

    Article  CAS  Google Scholar 

  5. C. Evangelisti, N. Panziera, P. Pertici, G. Vitulli, P. Salvadori, C. Battocchio, G. Polzonetti, J. Catal. 262, 287 (2009)

    Article  CAS  Google Scholar 

  6. C. Luo, Y. Zhang, Y. Wang, J. Mol. Catal. A Chem. 229, 7 (2005)

    Article  CAS  Google Scholar 

  7. R. Redona, N.G. GarciaPena, V.M.U. Saldivar, J.J. Garcia, J. Mol. Catal. A Chem. 300, 132 (2009)

    Article  Google Scholar 

  8. F. Zhao, B.M. Bhanage, M. Shirai, M. Arai, J. Mol. Catal. A Chem. 142, 383 (1999)

    Article  CAS  Google Scholar 

  9. A. Alimardanov, L.S. Vondervoort, A.H.M. Vries, J.G. Vries, Adv. Synth. Catal. 346, 1812 (2004)

    Article  CAS  Google Scholar 

  10. M.T. Reetz, J.G. Vries, Chem. Commun. 14, 1559 (2004)

    Article  Google Scholar 

  11. C. Amatore, A. Jutand, Acc. Chem. Res. 33, 314 (2000)

    Article  CAS  Google Scholar 

  12. C. Rocaboy, J.A. Gladysz, Org. Lett. 4, 1993 (2002)

    Article  CAS  Google Scholar 

  13. R. Javad Kalbasi, N. Mosaddegh, A. Abbaspourrad, Tetrahedron Lett. 53, 3763 (2012)

    Article  Google Scholar 

  14. D.M. Ford, E.E. Simanek, D.F. Shantz, Nanotechnology 16, S458 (2005)

    Article  Google Scholar 

  15. F. Hoffmann, M. Cornelius, J. Morell, M. Froba, Angew. Chem. Int. Ed. 45, 3216 (2006)

    Article  CAS  Google Scholar 

  16. K. Moller, T. Bein, Chem. Mater. 10, 2950 (1998)

    Article  CAS  Google Scholar 

  17. A. Taguchi, F. Schüth, Microporous Mesoporous Mater. 77, 1–45 (2004)

    Article  Google Scholar 

  18. U. Ciesla, F. Schüth, Microporous Mesoporous Mater. 27, 131 (1999)

    Article  CAS  Google Scholar 

  19. A. Corma, Chem. Rev. 97, 2373 (1997)

    Article  CAS  Google Scholar 

  20. M.E. Davis, Nature 417, 813 (2002)

    Article  CAS  Google Scholar 

  21. F. Schüth, W. Schmidt, Adv. Mater. 14, 629 (2002)

    Article  Google Scholar 

  22. J.C. Hicks, C.W. Jones, Langmuir 22, 2676 (2006)

    Article  CAS  Google Scholar 

  23. H. Li, J. Lü, Z. Zheng, R. Cao, J. Colloid Interface Sci. 353, 149 (2011)

    Article  CAS  Google Scholar 

  24. M. Bhagiyalakshmi, S.D. Park, W.S. Cha, H.T. Jang, Appl. Surf. Sci. 256, 6660 (2010)

    Article  CAS  Google Scholar 

  25. A. Shahbazi, H. Younesi, A. Badiei, Chem. Eng. J. 168, 505 (2011)

    Article  CAS  Google Scholar 

  26. A. Alizadeh, M.M. Khodaei, D. Kordestani, A.H. Fallah, M. Beygzadeh, Microporous Mesoporous Mater. 159, 9 (2012)

    Article  CAS  Google Scholar 

  27. A. Alizadeh, M.M. Khodaei, D. Kordestani, A.H. Fallah, M. Beygzadeh, J. Mol. Catal. A Chem. 372, 167 (2013)

    Article  CAS  Google Scholar 

  28. D.Y. Zhao, Q.S. Huo, J.L. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998)

    Article  CAS  Google Scholar 

  29. H. Veisi, Synthesis 42, 2631 (2010)

  30. H. Veisi, Tetrahedron Lett. 51, 2109 (2010)

    Article  CAS  Google Scholar 

  31. H. Veisi, Curr. Org. Chem. 15, 2438 (2011)

    Article  CAS  Google Scholar 

  32. W.J. Jones, W.J. Orville-Thomas, Trans. Faraday Soc. 55, 203 (1959)

    Article  CAS  Google Scholar 

  33. P.J. Larkin, M.P. Makowski, N.B. Colthup, L.A. Flood, Vib. Spectrosc. 17, 53 (1998)

    Article  CAS  Google Scholar 

  34. A.D. Becke, J. Chem. Phys. 104, 1040 (1996)

    Article  CAS  Google Scholar 

  35. N. Iranpoor, H. Firouzabadi, A. Tarassoli, M. Fereidoonnezhad, Tetrahedron 66, 2415 (2010)

    Article  CAS  Google Scholar 

  36. W. Prukala, M. Majchrzak, C. Pietraszuk, B. Marciniec, J. Mol. Catal. A Chem. 254, 58 (2006)

    Article  CAS  Google Scholar 

  37. W. Zhang, H. Qi, L. Li, X. Wang, J. Chen, K. Peng, Z. Wang, Green Chem. 11, 1194 (2009)

    Article  CAS  Google Scholar 

  38. K. Khler, R.G. Heidenreich, J.G.E. Krauter, J. Pietsch, Chem. Eur. J. 8, 622 (2002)

    Article  Google Scholar 

  39. Z. Wang, P. Xiao, B. Shen, N. He, Colloids Surf. A 276, 116 (2006)

    Article  CAS  Google Scholar 

  40. K. Qiao, R. Sugimura, Q. Bao, D. Tomida, C. Yokoyama, Catal. Commun. 9, 2470 (2008)

    Article  CAS  Google Scholar 

  41. S. Jana, B. Dutta, R. Bera, S. Koner, Inorg. Chem. 47, 5512 (2008)

    Article  CAS  Google Scholar 

  42. Y. Na, S. Park, S.B. Han, H. Han, S. Ko, S. Chang, J. Am. Chem. Soc. 126, 250 (2004)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are appreciates the Payame Noor University (PNU) for their partial support on this project.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hojat Veisi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 434 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Veisi, H., Kordestani, D. & Faraji, A.R. Palladium nanoparticles supported on an organosuperbase denderon-modified mesoporous SBA-15 as a heterogeneous catalyst in Heck coupling reaction. J Porous Mater 21, 141–148 (2014). https://doi.org/10.1007/s10934-013-9758-3

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-013-9758-3

Keywords

Navigation