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Synthesis of a novel Pd supported polymeric magnetic nanoparticles with urea-pyridine bridge: application as an efficient catalyst for the C–C and C–N bond formation

  • Fereshteh Heydari
  • Akbar MobinikhalediEmail author
  • Mohammad Ali Zolfigol
Article
  • 12 Downloads

Abstract

Here a novel Pd supported polymeric magnetic nanoparticles with urea-pyridine bridge (denoted as Fe3O4@/Urea-Pyridine/Pd) was synthesized and characterized. The Fe3O4@/Urea-Pyridine/Pd nanocatalyst was synthesized via a four steps process by using Fe3O4 nanoparticles, 3‐(triethoxysilyl) propylisocyanate (TESPIC), 2,6 bis(propyl-triethoxysilylureylene) pyridine (BPS) and palladium chloride. The synthesized polymeric Fe3O4@/Urea-Pyridine/Pd nanocatalyst was analyzed through different analytical techniques, including FT-IR, NMR, XRD, VSM, TGA, DTA, ICP, FESEM, EDX, and BET. The described palladium supported polymeric magnetic nanoparticles with urea-pyridine bridge (Pd-MNPs) was used for the C–C and C–N coupling of phenylboronic acid with various amines and aryl halides in DMF as well as Sonogashira and Suzuki reactions in aqueous solution. Also, the Fe3O4@/Urea-Pyridine/Pd nanocatalyst exhibited high structural stability and excellent recyclability.

Keywords

C–C coupling C–N coupling Magnetic nanoparticle Polymeric magnetic nanoparticles Sonogashira reaction Suzuki reaction 3‐(Triethoxysilyl) propylisocyanate 

Notes

Acknowledgements

We thank Arak University and Bu-Ali Sina University for financial support. Also, authors gratefully acknowledge Dr. L. Mohammadi and Dr. M. Yari for their guiding in the course of this research.

Supplementary material

10934_2019_820_MOESM1_ESM.docx (277 kb)
Supplementary material 1 (DOCX 277 kb)

References

  1. 1.
    L. Yin, Y. Liebscher, J. Chem. Rev. 107, 133 (2007)CrossRefGoogle Scholar
  2. 2.
    W. Li, Y. Tian, B. Zhang, L. Tian, X. Li, H. Zhang, N. Ali, Q. Zhang, New J. Chem. 39, 2767 (2015)CrossRefGoogle Scholar
  3. 3.
    R. Jahanshahi, B. Akhlaghinia, Catal Lett. 147, 2640 (2017)CrossRefGoogle Scholar
  4. 4.
    E. Mulahmetovic, G.C. Hargaden, Rev. J. Chem. 7, 373 (2017)CrossRefGoogle Scholar
  5. 5.
    N.Y. Baran, T. Baran, A. Menteş, Carbohydr. Polym. 181, 596 (2018)CrossRefPubMedPubMedCentralGoogle Scholar
  6. 6.
    A.Y. Mitrofanov, A.V. Murashkina, I.M. García, F. Alonso, I.P. Beletskaya, Catal. Sci. Technol. 7, 4401 (2017)CrossRefGoogle Scholar
  7. 7.
    N. Kambe, T. Iwasakia, J. Terao, Chem. Soc. Rev. 40, 4937 (2011)CrossRefPubMedPubMedCentralGoogle Scholar
  8. 8.
    A. Mobinikhaledi, H. Moghanian, S.M.B.H. Ghazvini, A. Dalvand, J. Porous. Mater. 25, 1123 (2018)CrossRefGoogle Scholar
  9. 9.
    A. Majumder, R. Gupta, M. Mandal, M. Babu, D. Chakraborty, J. Organomet. Chem. 781, 23 (2015)CrossRefGoogle Scholar
  10. 10.
    M. Esmaeilpour, A.R. Sardarian, J. Javidi, J. Organomet. Chem. 749, 233e (2014)CrossRefGoogle Scholar
  11. 11.
    J.H. Cho, K.H. Shaughnessy, Synlett 20, 2963 (2011)Google Scholar
  12. 12.
    X.J. Feng, M. Yan, T. Zhang, Y. Liu, M. Bao, Green Chem. 12, 1758 (2010)CrossRefGoogle Scholar
  13. 13.
    J. Zhang, G.F. Zhao, Z. Popovic, Y. Lu, Y. Liu, Mater. Res. Bull. 45, 1648 (2010)CrossRefGoogle Scholar
  14. 14.
    S. Rana, S. Maddila, K. Yalagala, S.B. Jonnalagadda, Appl Catal. A. 505, 539 (2015)CrossRefGoogle Scholar
  15. 15.
    F. Yang, C. Chi, S. Dong, C. Wang, X. Jia, L. Ren, Y. Zhang, L. Zhang, Y. Li, Catal. Today 256, 186 (2015)CrossRefGoogle Scholar
  16. 16.
    F. Yang, Y.F. Li, T. Liu, K. Xu, L.Q. Zhang, C.M. Xu, J.S. Gao, Chem. Eng. J. 226, 52 (2013)CrossRefGoogle Scholar
  17. 17.
    D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)CrossRefGoogle Scholar
  18. 18.
    V. Polshettiwar, R. Luque, A. Fihri, H.B. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)CrossRefGoogle Scholar
  19. 19.
    M. Afradi, N. Foroughifar, H. Pasdar, H. Moghanian, Appl. Organomet. Chem. 31, e3683 (2017)CrossRefGoogle Scholar
  20. 20.
    H. Moghanian, M.A Bodaghi Fard, A. Mobinikhaledi, N. Ahad, Res. Chem. Intermed. 44, 4083 (2018)CrossRefGoogle Scholar
  21. 21.
    A.M. Bonilla, P.H. González, Curr. Pharm. Des. 23, 5392 (2017)PubMedGoogle Scholar
  22. 22.
    L. Mohammed, D. Ragab, H. Gomaa, Curr. Pharm. Des. 22, 3332 (2016)CrossRefGoogle Scholar
  23. 23.
    S.D. Xiang, C. Selomulya, J. Ho, V. Apostolopoulos, M. Plebanski, Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol. 2, 205 (2010)CrossRefGoogle Scholar
  24. 24.
    A. Pourjavadi, M. Tajbakhsh, M. farhang, S. H. Hosseini, New J. Chem. 39, 4591 (2015)CrossRefGoogle Scholar
  25. 25.
    J. Wang, B. Xu, H. Sun, G. Song, Tetrahedron Lett. 54, 238 (2013)CrossRefGoogle Scholar
  26. 26.
    T. Azadbakht, M.A. Zolfigol, R. Azadbakht, V. Khakyzadeh, D.M. Perrin, New J. Chem. 39, 439 (2015)CrossRefGoogle Scholar
  27. 27.
    M.A. Zolfigol, T. Azadbkht, V. Khakizadeh, R. Nejatyami, D. Perrin, RSC. Adv. 4, 40036 (2014)CrossRefGoogle Scholar
  28. 28.
    M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M.H. Beyzavie, R. Luque, Green Chem. 15, 2132 (2013)CrossRefGoogle Scholar
  29. 29.
    M. Aghayee, M.A. Zolfigol, H. Keypoura, M. Yarie, L. Mohammadi, Appl. Organomet. Chem. 30, 612 (2016)CrossRefGoogle Scholar
  30. 30.
    A. Ghorbani-Choghamarani, M. Mohammadi, Z. Taherinia, J. Iran Chem. Soc. 16, 411 (2019)CrossRefGoogle Scholar
  31. 31.
    M.M. Heravi, Z. Kheilkordi, V. Zadsirjan, M. Heydari, M. Malmir, J. Organomet. Chem. 861, 17 (2018)CrossRefGoogle Scholar
  32. 32.
    M. Nasrollahzadeh, M. Atarod, M. Alizadeh, A. Hatamifard, S.M. Sajadi, Curr. Org. Chem. 21, 708 (2017)CrossRefGoogle Scholar
  33. 33.
    B. Karimi, F. Mansouri, H.M. Mirzaei, Chem Cat. Chem. 7, 1736 (2015)Google Scholar
  34. 34.
    F. Liu, L. Fu, J. Wang, Q. Meng, H. Li, J. Guo, H. Zhang, New J. Chem. 27, 233 (2003)CrossRefGoogle Scholar
  35. 35.
    P. Borah, J. Mondal, Y. Zhao, J. Catal. 330, 129 (2015)CrossRefGoogle Scholar
  36. 36.
    B. Atashkara, M.A. Zolfigol., S. Mallakpour, Mol. Catal. 452, 192 (2018)CrossRefGoogle Scholar
  37. 37.
    S. Baghery, M.A. Zolfigol, R. Schirhagl, M. Hasani, M.C.A. Stuart, A. Nagl, Appl. Organometal Chem. 31, e3883 (2017)CrossRefGoogle Scholar
  38. 38.
    S. Qu, H. Yang, D. Ren, S. Kan, G. Zou, D. Li, M. Li, J. Colloid Interface Sci. 215, 190 (1999)CrossRefPubMedPubMedCentralGoogle Scholar
  39. 39.
    L. Mohammadi, M.A. Zolfigol, A. Khazaei, M. Yarie, S. Ansari, S. Azizian, M. Khosravi, Appl. Organomet. Chem. 32, e3933 (2017)CrossRefGoogle Scholar
  40. 40.
    I.P. Beletskaya, A.V. Cheprakov, Organometal. 31, 7753 (2012)CrossRefGoogle Scholar
  41. 41.
    L. Kurti, B. Czako. Elsevier Academic Press (2005)Google Scholar
  42. 42.
    R.R. Jadhav, S.N. Huddar, K.G. Akamanchi, Eur. J. Org. Chem. 30, 6779 (2013)CrossRefGoogle Scholar
  43. 43.
    Q. Yang, X. Lei, Z. Yin, Z. Deng, Y. Peng, Synthesis 51, 538 (2019)CrossRefGoogle Scholar
  44. 44.
    Q.L. Shao, Z.J. Jiang, W.K. Su, Tetrahedron Lett. 23, 2277 (2018)CrossRefGoogle Scholar
  45. 45.
    D. Koseki, E. Aoto, T. Shoji, K. Watanabe, Y. In, Y. Kita, T. Dohi, Tetrahedron Lett. 18, 1281 (2019)CrossRefGoogle Scholar
  46. 46.
    H. Chen, M. Lei, L. Hu, Tetrahedron 70, 5626 (2014)CrossRefGoogle Scholar
  47. 47.
    X. Hong, Q. Tan, B. Liu, B. Xu, Angew. Chem. 14, 4019 (2017)CrossRefGoogle Scholar
  48. 48.
    N. Hussain, P. Gogoi, P. Khare, M.R. Das, RSC Adv. 5, 103105 (2015)CrossRefGoogle Scholar
  49. 49.
    F. Chang, Y. Liu, Synth. Commun. 47, 961 (2017)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceArak UniversityArakIran
  2. 2.Department of Organic Chemistry, Faculty of ChemistryBu-Ali Sina UniversityHamedanIran

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