Skip to main content
Log in

Pd(II)/Pd(0) Anchored on Magnetic Organic–Inorganic Hybrid Mesoporous Silica Nanoparticles: A Nanocatalyst for Suzuki–Miyaura and Heck–Mizoroki Coupling Reactions

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

3-Chloropropyltrimethoxysilane (CPTMS) was grafted on the surface of silica coated Fe3O4 core (Fe3O4@MCM-41) and then condensed with thiocarbohydrazide (TCH) to obtain Fe3O4@MCM-41-CPS-TCH. Then the heterogeneous Fe3O4@MCM-41-CPS-TCH-Pd nanocatalyst was synthesized by adding palladium(II) chloride to functionalized Fe3O4@MCM-41. The resultant nanomaterials were characterized using several techniques such as FT-IR, XRD, FE-SEM, HRTEM, EDS, BET, VSM, XPS, AAS and TGA. Then, the efficiency of this Palladium based magnetic nanocomposite was examined as catalyst for the preparation of biaryl derivatives using the Suzuki coupling of phenylboronic acid with various aryl halides in H2O/EtOH as a green solvent. The as-synthesized nanocomposite was also checked for the Heck–Mizoroki coupling reaction of various aryl halides and styrene. This catalytic system was easily retrieved by a magnetic field and reused for several times without distinct reduction in 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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. S. Nishimura, K. Ebitani, ChemCatChem 8, 2303–2316 (2016)

    Article  CAS  Google Scholar 

  2. A. Molnar, Chem. Rev. 111, 2251–2320 (2011)

    Article  CAS  PubMed  Google Scholar 

  3. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 102, 1359–1470 (2002)

    Article  CAS  PubMed  Google Scholar 

  4. E. Mulahmetovic, G. Hargaden, Rev. J. Chem. 7, 373–398 (2017)

    Article  CAS  Google Scholar 

  5. D. Astruc, Inorg. Chem. 46, 1884–1894 (2007)

    Article  CAS  PubMed  Google Scholar 

  6. G. Borah, D. Boruah, G. Sarmah, S.K. Bharadwaj, U. Bora, Appl. Organomet. Chem. 27, 688–694 (2013)

    Article  CAS  Google Scholar 

  7. B. Milde, D. Schaarschmidt, T. Rüffer, H. Lang, Dalton Trans. 41, 5377–5390 (2012)

    Article  CAS  PubMed  Google Scholar 

  8. N. Biricik, F. Durap, C. Kayan, B. Gümgüm, N. Gürbüz, İ Özdemir, W.H. Ang, Z. Fei, R. Scopelliti, J. Organomet. Chem. 693, 2693–2699 (2008)

    Article  CAS  Google Scholar 

  9. P. Das, C. Sarmah, A. Tairai, U. Bora, Appl. Organomet. Chem. 25, 283–288 (2011)

    Article  CAS  Google Scholar 

  10. S. Layek, B. Agrahari, D.D. Pathak, J. Organomet. Chem. 846, 105–112 (2017)

    Article  CAS  Google Scholar 

  11. Z. Mandegani, M. Asadi, Z. Asadi, A. Mohajeri, N. Iranpoor, A. Omidvar, Green Chem. 17, 3326–3337 (2015)

    Article  CAS  Google Scholar 

  12. L. Wang, S. Xu, S. He, F.-S. Xiao, Nano Today 20, 74–83 (2018)

    Article  CAS  Google Scholar 

  13. J. Hu, Q. Wu, K. Li, W. Li, F. Ma, S. Zhang, F. Su, Y. Guo, Y. Wang, Catal. Commun. 12, 238–242 (2010)

    Article  CAS  Google Scholar 

  14. B. Altava, M.I. Burguete, E. García-Verdugo, S.V. Luis, Chem. Soc. Rev. 47, 2722–2771 (2018)

    Article  CAS  PubMed  Google Scholar 

  15. M. Sarvestani, R. Azadi, Can. J. Chem. 97, 191–196 (2019)

    Article  CAS  Google Scholar 

  16. S.B. Singh, P.K. Tandon, J. Energy Chem. Eng. 2, 106–115 (2014)

    Google Scholar 

  17. G.A. Somorjai, H. Frei, J.Y. Park, J. Am. Chem. Soc. 131, 16589–16605 (2009)

    Article  CAS  PubMed  Google Scholar 

  18. J. Li, H. Ji, Y. Xu, J. Zhang, Y. Yan, J. Mater. Res. Technol. 9, 762–772 (2020)

    Article  CAS  Google Scholar 

  19. G. Ro, D.K. Hwang, Y. Kim, J. Ind. Eng. Chem. 79, 364–369 (2019)

    Article  CAS  Google Scholar 

  20. R.M. Bezerra, R.R.C. Monteiro, D.M.A. Neto, F.F.M. da Silva, R.C.M. de Paula, T.L.G. de Lemos, P.B.A. Fechine, M.A. Correa, F. Bohn, L.R.B. Gonçalves, J.C.S. dos Santos, Enzym. Microb. Technol. 138, 109560 (2020)

    Article  CAS  Google Scholar 

  21. S. Kargar, D. Elhamifar, A. Zarnegaryan, J. Phys. Chem. Solids 146, 109601 (2020)

    Article  CAS  Google Scholar 

  22. G.U. Rehman, M. Tahir, P.S. Goh, A.F. Ismail, I.U. Khan, Powder Technol. 356, 547–558 (2019)

    Article  CAS  Google Scholar 

  23. W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. N.C.C. Lobato, A. de Mello Ferreira, P.G. Weidler, M. Franzreb, M.B. Mansur, Sep. Purif. Technol. 229, 115839 (2019)

    Article  CAS  Google Scholar 

  25. E. Taşçı, S. Akbayrak, S. Özkar, Int. J. Hydrogen Energy 43, 15124–15134 (2018)

    Article  CAS  Google Scholar 

  26. I. Dayana, T. Sembiring, A.P. Tetuko, K. Sembiring, N. Maulida, Z. Cahyarani, E.A. Setiadi, N.S. Asri, M. Ginting, P. Sebayang, J. Mol. Liq. 294, 111557 (2019)

    Article  CAS  Google Scholar 

  27. N. Esfandiari, M. Kashefi, M. Mirjalili, S. Afsharnezhad, Mater Sci Eng B 262, 114690 (2020)

    Article  CAS  Google Scholar 

  28. A. Ahmadi, T. Sedaghat, H. Motamedi, R. Azadi, Appl. Organomet. Chem. 34, e5572 (2020)

    Article  CAS  Google Scholar 

  29. Z. Zhu, W. Wang, L. Zeng, F. Zhang, J. Liu, Catal. Commun. 142, 106031 (2020)

    Article  CAS  Google Scholar 

  30. M. Hachemaoui, A. Mokhtar, A. Mekki, F. Zaoui, S. Abdelkrim, S. Hacini, B. Boukoussa, Int. J. Biol. Macromol. 164, 468–479 (2020)

    Article  CAS  PubMed  Google Scholar 

  31. A. Ulu, I. Ozcan, S. Koytepe, B. Ates, Int. J. Biol. Macromol. 115, 1122–1130 (2018)

    Article  CAS  PubMed  Google Scholar 

  32. W. Xie, Y. Han, H. Wang, Renew. Energy 125, 675–681 (2018)

    Article  CAS  Google Scholar 

  33. C.-H. Lee, T.-S. Lin, C.-Y. Mou, Nano Today 4, 165–179 (2009)

    Article  CAS  Google Scholar 

  34. P. Zucca, E. Sanjust, Molecules 19, 14139–14194 (2014)

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  35. M.L. Cacicedo, R.M. Manzo, S. Municoy, H.L. Bonazza, G.A. Islan, M. Desimone, M. Bellino, E.J. Mammarella, G.R. Castro, Chapter 7—immobilized enzymes and their applications, in Advances in Enzyme Technology. ed. by R.S. Singh, R.R. Singhania, A. Pandey, C. Larroche (Elsevier, Amsterdam, 2019), pp. 169–200

    Chapter  Google Scholar 

  36. L. Tahmasbi, T. Sedaghat, H. Motamedi, M. Kooti, J. Solid State Chem. 258, 517–525 (2018)

    Article  CAS  Google Scholar 

  37. A. Ahmadi, T. Sedaghat, R. Azadi, H. Motamedi, Catal. Lett. 150, 112–126 (2020)

    Article  CAS  Google Scholar 

  38. J. Zhu, J. He, X. Du, R. Lu, L. Huang, X. Ge, Appl. Surf. Sci. 257, 9056–9062 (2011)

    Article  CAS  Google Scholar 

  39. M. Khosroshahi, L. Ghazanfari, Phys. E 42, 1824–1829 (2010)

    Article  CAS  Google Scholar 

  40. M. Kooti, M. Afshari, Mater. Res. Bull. 47, 3473–3478 (2012)

    Article  CAS  Google Scholar 

  41. Y. Wang, B. Li, L. Zhang, P. Li, L. Wang, J. Zhang, Langmuir 28, 1657–1662 (2012)

    Article  CAS  PubMed  Google Scholar 

  42. Y. Cai, L. Ling, X. Li, M. Chen, L. Su, J. Solid State Chem. 226, 179–185 (2015)

    Article  CAS  Google Scholar 

  43. H. Fu, Y. Chen, H. Zhang, Y. Wang, M. Zhang, P. Hu, J. Nanosci. Nanotechnol. 17, 3077–3083 (2017)

    Article  CAS  Google Scholar 

  44. J. Jang, H. Lim, Microchem. J. 94, 148–158 (2010)

    Article  CAS  Google Scholar 

  45. Y. Wang, B. Li, L. Zhang, H. Song, Langmuir 29, 1273–1279 (2013)

    Article  CAS  PubMed  Google Scholar 

  46. G. Zhang, P. Wang, X. Wei, Catal. Lett. 143, 1188–1194 (2013)

    Article  CAS  Google Scholar 

  47. T. Baran, Int. J. Biol. Macromol. 127, 232–239 (2019)

    Article  CAS  PubMed  Google Scholar 

  48. N. Gogoi, U. Bora, G. Borah, P.K. Gogoi, Appl. Organomet. Chem. 31, e3686 (2017)

    Article  CAS  Google Scholar 

  49. D. Tang, L. Zhang, Y. Zhang, Z.-A. Qiao, Y. Liu, Q. Huo, J. Colloid Interface Sci. 369, 338–343 (2012)

    Article  CAS  PubMed  Google Scholar 

  50. D. Zhang, X. Wang, Z.-A. Qiao, D. Tang, Y. Liu, Q. Huo, J. Phys. Chem. C 114, 12505–12510 (2010)

    Article  CAS  Google Scholar 

  51. C.-C. Liu, T.-S. Lin, S.I. Chan, C.-Y. Mou, J. Catal. 322, 139–151 (2015)

    Article  CAS  Google Scholar 

  52. A.K. Rathi, M.B. Gawande, J. Pechousek, J. Tucek, C. Aparicio, M. Petr, O. Tomanec, R. Krikavova, Z. Travnicek, R.S. Varma, Green Chem. 18, 2363–2373 (2016)

    Article  CAS  Google Scholar 

  53. F.D. Firuzabadi, Z. Asadi, F. Panahi, RSC Adv. 6, 101061–101070 (2016)

    Article  CAS  Google Scholar 

  54. M. Tukhani, F. Panahi, A. Khalafi-Nezhad, ACS Sustain. Chem. Eng. 6, 1456–1467 (2017)

    Article  CAS  Google Scholar 

  55. G. Azadi, A. Ghorbani-Choghamarani, Appl. Organomet. Chem. 30, 360–366 (2016)

    Article  CAS  Google Scholar 

  56. M. Esmaeilpour, J. Javidi, J. Chin. Chem. Soc. 62, 614–626 (2015)

    Article  CAS  Google Scholar 

  57. M. Khanmoradi, M. Nikoorazm, A. Ghorbani-Choghamarani, Catal. Lett. 147, 1114–1126 (2017)

    Article  CAS  Google Scholar 

  58. J. Chen, J. Zhang, D. Zhu, T. Li, Appl. Organomet. Chem. 32, e3996 (2018)

    Google Scholar 

  59. A.R. Hajipour, A.R. Sadeghi, Z. Khorsandi, Appl. Organomet. Chem. 32, e4112 (2018)

    Article  CAS  Google Scholar 

  60. S. Sobhani, S. Esmaeilzadeh-Soleimani, Org. Chem. Res. 5, 10–24 (2019)

    Google Scholar 

  61. E. Rezapour, M. Jafarpour, A. Rezaeifard, Catal. Lett. 148, 3165–3177 (2018)

    Article  CAS  Google Scholar 

  62. F.R. Fortea-Pérez, I. Schlegel, M. Julve, D. Armentano, G. De. Munno, S.-E. Stiriba, J. Organomet. Chem. 743, 102–108 (2013)

    Article  CAS  Google Scholar 

  63. A.S. Singh, U.B. Patil, J.M. Nagarkar, Catal. Commun. 35, 11–16 (2013)

    Article  CAS  Google Scholar 

  64. S.S. Shendage, A.S. Singh, J.M. Nagarkar, Tetrahedron Lett. 55, 857–860 (2014)

    Article  CAS  Google Scholar 

  65. A. Naghipour, A. Fakhri, Catal. Commun. 73, 39–45 (2016)

    Article  CAS  Google Scholar 

  66. S.J. Hoseini, V. Heidari, H. Nasrabadi, J. Mol. Catal. A 396, 90–95 (2015)

    Article  CAS  Google Scholar 

  67. M. Nasrollahzadeh, A. Azarian, A. Ehsani, M. Khalaj, J. Mol. Catal. A 394, 205–210 (2014)

    Article  CAS  Google Scholar 

  68. M. Zhu, G. Diao, J. Phys. Chem. C 115, 24743–24749 (2011)

    Article  CAS  Google Scholar 

  69. H. Veisi, N. Mirzaee, Appl. Organomet. Chem. 32, e4067 (2018)

    Article  CAS  Google Scholar 

  70. H. Veisi, A. Sedrpoushan, S. Hemmati, Appl. Organomet. Chem. 29, 825–828 (2015)

    Article  CAS  Google Scholar 

  71. A. Papp, G. Galbács, Á. Molnár, Tetrahedron Lett. 46, 7725–7728 (2005)

    Article  CAS  Google Scholar 

  72. A. Khalafi-Nezhad, F. Panahi, ACS Sustain. Chem. Eng. 2, 1177–1186 (2014)

    Article  CAS  Google Scholar 

  73. A. Nuri, Y. Mansoori, A. Bezaatpour, Appl. Organomet. Chem. 33, e4904 (2019)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Support of this work by Shahid Chamran University of Ahvaz, Ahvaz, Iran (Grant No. SCU.SC98.835) is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Tahereh Sedaghat.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ahmadi, A., Sedaghat, T. & Azadi, R. Pd(II)/Pd(0) Anchored on Magnetic Organic–Inorganic Hybrid Mesoporous Silica Nanoparticles: A Nanocatalyst for Suzuki–Miyaura and Heck–Mizoroki Coupling Reactions. J Inorg Organomet Polym 31, 4126–4140 (2021). https://doi.org/10.1007/s10904-021-02045-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-021-02045-7

Keywords

Navigation