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Fe3O4@SiO2-polymer-imid-Pd magnetic porous nanosphere as magnetically separable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions

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Abstract

The activity of palladium nanoparticles supported on poly (N-vinylpyrrolidone) grafted Fe3O4@SiO2 was investigated in the cross-coupling reactions. We have applied this catalyst under low loading of the supported palladium nanoparticles for the coupling of aryl halides with alkenes (Mizoroki–Heck reaction) and organoboronic acids (Suzuki–Miyaura reaction) in the absence of phosphorous ligands. Short reaction times and excellent yields of the products express the effectiveness of this catalyst. The nanocatalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused for six times without appreciable change in catalytic activity. Also, the amount of leaching of Pd nanoparticles has been determined by ICP analysis and results showed low leaching of the metal into solution from the supported catalyst.

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References

  1. L. Yin, J. Liebsher, Chem. Rev. 107, 133 (2007)

    Article  CAS  Google Scholar 

  2. R. Kore, M. Tumma, R. Srivastava, Catal. Today 198, 189 (2012)

    Article  CAS  Google Scholar 

  3. B. Tamami, F. Farjadian, J. Iran. Chem. Soc. 8, 77 (2011)

    Article  Google Scholar 

  4. N.T.S. Phan, M.V. Der Sluys, C.W. Jones, Adv. Synth. Catal. 348, 609 (2006)

    Article  CAS  Google Scholar 

  5. S.G. Ryu, S.W. Kim, S.D. Oh, S.H. Choi, H.G. Park, Y.P. Zhang, Colloid. Surface A. 313, 224 (2008)

    Article  Google Scholar 

  6. Kh Niknam, A. Deris, F. Panahi, M.R. Hormozi, Nezhad. J. Iran. Chem. Soc. 10, 1291 (2013)

    Article  CAS  Google Scholar 

  7. 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)

    Article  CAS  Google Scholar 

  8. V. Polshettiwar, A. Molnar, Tetrahedron 63, 6949 (2007)

    Article  CAS  Google Scholar 

  9. B. Tamami, F. Nowroozi, Dodeji. J. Iran. Chem. Soc. 9, 841 (2012)

    Article  CAS  Google Scholar 

  10. A.J. Amali, R.K. Rana, Green Chem. 11, 1781 (2009)

    Article  CAS  Google Scholar 

  11. V. Kogan, Z. Aizenshtat, R. Popovitz-Biro, R. Neumann, Org. Lett. 4, 3529 (2002)

    Article  CAS  Google Scholar 

  12. L. Brandsma, S.F. Vasilersky, H.D. Verkruijsse, Applications of transition metal catalysts in organic synthesis (Springer, Berlin, 1988)

    Google Scholar 

  13. R.F. Heck, Org. React. 27, 345 (1982)

    CAS  Google Scholar 

  14. I.P. Beletskaya, A.V. Cheprakov, Chem. Rev. 100, 3009 (2000)

    Article  CAS  Google Scholar 

  15. N.J. Whitcombe, K.K. Hii, S.E. Gibson, Tetrahedron 57, 7449 (2001)

    Article  CAS  Google Scholar 

  16. M. Bagherzadeh, M. Amini, A. Ellern, L.K. Woo, Inorg. Chim. Acta 383, 46 (2012)

    Article  CAS  Google Scholar 

  17. A. Suzuki, J. Organomet. Chem. 576, 147 (1999)

    Article  CAS  Google Scholar 

  18. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 58, 9633 (2002)

    Article  CAS  Google Scholar 

  19. S.P. Stanforth, Tetrahedron 54, 263 (1998)

    Article  CAS  Google Scholar 

  20. K.H. Niknam, Habibabad, A. Deris, F. Panahi, M.R.H. Nezhad, J. Iran. Chem. Soc. 10, 527 (2013)

    Article  CAS  Google Scholar 

  21. G. Mengping, Zh Zhiyong, H. Hongwei, Zh Qiaochu, Catal. Commun. 10, 865 (2009)

    Article  Google Scholar 

  22. R. Chinchilla, C. Najera, M. Yus, Chem. Rev. 104, 2667 (2004)

    Article  CAS  Google Scholar 

  23. T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem. 70, 2191 (2005)

    Article  CAS  Google Scholar 

  24. T.J. Colacot, H.A. Shea, Org. Lett. 6, 3731 (2004)

    Article  CAS  Google Scholar 

  25. N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, J. Organomet. Chem. 708, 118 (2012)

    Article  Google Scholar 

  26. E. Mieczynska, A. Gniewek, I. Pryjomska-Ray, A.M. Trzeciak, H. Grabowska, M. Zawadzki, Appl. Catal A-Gen. 393, 195 (2011)

    Article  CAS  Google Scholar 

  27. B. Punji, C. Ganesamoorthy, M.S. Balakrishna, J. Mol. Catal. A-Chem. 259, 78 (2006)

    Article  CAS  Google Scholar 

  28. S. Blügel, T. Brückel, C.M. Schneider, Magnetism goes nano: electron correlations, spin transport, molecular magnetism (2005)

  29. H. Kronmüller, S. Parkin, Handbook of magnetism and advanced magnetic materials (Wiley, Hoboken, 2007)

    Book  Google Scholar 

  30. B.D. Terris, T. Thomson, J. Phys. D: Appl. Phys. 38, 199 (2005)

    Article  Google Scholar 

  31. O. Petracic, Superlattice. Microst. 47, 569 (2010)

    Article  CAS  Google Scholar 

  32. D.K. Lee, Y.S. Kang, C.S. Lee, P. Stroeve, J. Phys. Chem. B. 106, 7267 (2002)

    Article  CAS  Google Scholar 

  33. D.H. Zhang, Z.Q. Liu, S. Han, C. Li, B. Lei, M.P. Stewart, Nano. Lett. 4, 2151 (2004)

    Article  CAS  Google Scholar 

  34. P.C. Wang, C.F. Lee, T.H. Young, D.T. Lin, W.Y. Chiu, J. Polym. Sci. Part. A. Polym. Chem. 43, 1342 (2005)

    Article  CAS  Google Scholar 

  35. S.T. Tan, J.H. Wendorff, C. Pietzonka, Z.H. Jia, G.Q. Wang, Chem. Phys. Chem. 6, 1461 (2005)

    CAS  Google Scholar 

  36. I. Garcia, N.E. Zafeiropoulos, A. Janke, A. Tercjak, A. Eceiza, M. Stamm, J. Polym. Sci. Part. A. Polym. Chem. 45, 925 (2007)

    Article  CAS  Google Scholar 

  37. A. Schatz, M. Hager, O. Reiser, Adv. Funct. Mater. 19, 2109 (2009)

    Article  Google Scholar 

  38. D.D. Shao, K.K. Xu, X.J. Song, J.H. Hu, W.L. Yang, C.C. Wang, J. Colloid, Interface. Sci. 336, 526 (2009)

    Article  CAS  Google Scholar 

  39. Y.H. Deng, D.W. Qi, C.H. Deng, X.M. Zhang, D.Y. Zhao, J. Am. Chem. Soc. 130, 28 (2008)

    Article  CAS  Google Scholar 

  40. Y. Akiyama, X. Meng, S. Fujita, Y.C. Chen, N. Lu, H. Cheng, F. Zhao, M. Arai, J. Supercrit. Fluid. 51, 209 (2009)

    Article  CAS  Google Scholar 

  41. M. Esmaeilpour, A.R. Sardarian, J. Javidi, Appl. Catal A-Gen. 445–446, 359 (2012)

    Article  Google Scholar 

  42. M. Esmaeilpour, J. Javidi, M.M. Abarghoui, F.N. Dodeji, J. Iran. Chem. Soc. (2013). doi:10.1007/s13738-013-0323-4

    Google Scholar 

  43. Zh Li, J. Chen, W. Su, M. Hong, J. Mol. Catal A: Chem. 328, 93 (2010)

    Article  CAS  Google Scholar 

  44. H. Firouzabadi, N. Iranpoor, A. Ghaderi, J. Mol. Catal. A: Chem. 347, 38 (2011)

    Article  CAS  Google Scholar 

  45. H. Firouzabadi, N. Iranpoor, F. Kazemi, M. Gholinejad, J. Mol. Catal A: Chem. 357, 154 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  47. N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, J. Organomet. Chem. 708–709, 118 (2012)

    Article  Google Scholar 

  48. B. Punji, C. Ganesamoorthy, M.S. Balakrishna, J. Mol. Catal A: Chem. 259, 78 (2006)

    Article  CAS  Google Scholar 

  49. B. Tamami, S. Ghasemi, J. Mol. Catal A: Chem. 322, 98 (2010)

    Article  CAS  Google Scholar 

  50. C. Pan, M. Liu, L. Zhang, H. Wu, J. Ding, J. Cheng, Catal. Commun. 9, 508 (2008)

    Article  CAS  Google Scholar 

  51. H. Firouzabadi, N. Iranpoor, M. Gholinejad, J. Organomet. Chem. 695, 2093 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Authors are grateful to the council of Iran National Science Foundation and University of Shiraz for their unending effort to provide financial support to undertake this work.

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Authors and Affiliations

  1. Chemistry Department, College of Science, Shiraz University, Shiraz, Iran

    Mohsen Esmaeilpour

  2. Department of Pharmaceutics, School of Pharmacy, Shaheed Beheshti University of Medical Sciences, Tehran, Iran

    Jaber Javidi & Fatemeh Nowroozi Dodeji

  3. Department of Chemistry, Payame Noor University, PO Box 74515-161, Estahban, Iran

    Hamed Hassannezhad

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  1. Mohsen Esmaeilpour
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  2. Jaber Javidi
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  3. Fatemeh Nowroozi Dodeji
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  4. Hamed Hassannezhad
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Correspondence to Jaber Javidi.

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Esmaeilpour, M., Javidi, J., Dodeji, F.N. et al. Fe3O4@SiO2-polymer-imid-Pd magnetic porous nanosphere as magnetically separable catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling reactions. J IRAN CHEM SOC 11, 1703–1715 (2014). https://doi.org/10.1007/s13738-014-0443-5

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