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MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates

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Abstract

Nanosize magnetic particles coated with magnesium oxide (core/shell nanoparticles) have been prepared and used for the synthesis of 1-hydroxyalkyl phosphonates. Catalytic activity studies show that the magnetic particles coated with magnesium oxide have highly catalytic activity toward the phosphorylation of aldehydes for the synthesis of 1-hydroxyalkyl phosphonates under solvent-free conditions. Reusability of the prepared magnetic nanoparticles was successfully examined five times with a very slight loss of catalytic activity.

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References

  1. K. Layek, H. Maheswaran, M.L. Kantam, Catal. Sci. Technol. 3, 1147–1150 (2013)

    Article  CAS  Google Scholar 

  2. A. Monopoli, P. Cotugno, G. Palazzo, N. Ditaranto, B. Mariano, N. Cioffi, F. Ciminale, A. Nacci, Adv. Synth. Catal. 354, 2777–2788 (2012)

    Article  CAS  Google Scholar 

  3. K. Layek, R. Chakravarti, M.L. Kantam, H. Maheswaran, A. Vinu, Green Chem. 13, 2878–2887 (2011)

    Article  CAS  Google Scholar 

  4. J. Chen, L.N. Xu, W.Y. Li, X.L. Gou, Adv. Mater. 17, 582–586 (2005)

    Article  CAS  Google Scholar 

  5. L. Yu, M. Wang, P. Li, L. Wang, Appl. Organomet. Chem. 26, 576–582 (2012)

  6. S.B. Simonsen, D. Chakraborty, I. Chrokendorff, S. Dahl, Appl. Catal. A 447–448, 22–31 (2012)

    Article  Google Scholar 

  7. B. Kaboudin, R. Mostafalu, T. Yokomatsu, Green Chem. 15, 2266–2274 (2013)

    Article  CAS  Google Scholar 

  8. Q. Zhang, H. Su, J. Luo, Y. Wei, Catal. Sci. Technol. 3, 235–243 (2013)

    Article  Google Scholar 

  9. Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 14, 201–208 (2012)

    Article  CAS  Google Scholar 

  10. L.D. Matteis, L. Custardoy, R. Fernandez-Pacheco, C. Magen, J.M. de la Fuente, C. Marquina, M.R. Ibarra, Chem. Mater. 24, 451–456 (2012)

    Article  Google Scholar 

  11. R.L. Hilderbrand, The Role of Phosphonates in Living Systems (CRC Press, Boca Raton, 1982)

  12. D. Redmore, in Topics in Phosphorus Chemistry, ed. by E.J. Griffith, M. Grayson, vol. 8 (Wiley, New York, 1976)

  13. K. Afarinkia, C.W. Rees, Tetrahedron 46, 7175–7196 (1990)

    Article  CAS  Google Scholar 

  14. B. Kaboudin, H. Haghighat, S. Alaie, T. Yokomatsu, Synlett 1965–1969 (2012)

  15. B. Kaboudin, M. Fallahi, Tetrahedron Lett. 52, 4346–4348 (2011)

    Article  CAS  Google Scholar 

  16. B. Kaboudin, Tetrahedron Lett. 44, 1051–1053 (2003)

    Article  CAS  Google Scholar 

  17. B. Kaboudin, M. Karimi, Bioorg. Med. Chem. Lett. 16, 5324–5327 (2006)

    Article  CAS  Google Scholar 

  18. B. Kaboudin, S. Emadi, M.R. Faghihi, M. Fallahi, V. Sheikh-Hasani, J. Enzym. Inhib. Med. Chem. 28, 576–582 (2013)

    Article  CAS  Google Scholar 

  19. V.S. Abramov, Dokl, Akad, Nauk, SSSR, 95, 991 (1954); Chem Abstr., 49 (1955), 32068

  20. A.N. Pudovik, B.A. Arbuzov, Dokl, Akad, Nauk, SSSR, 73, 327 (1950); Chem Abstr., 45 (1951), 16243

  21. M. Pandi, P.K. Chanani, S. Govindasamy, Appl. Catal. A Gener. 441–442 (2012)

  22. C. Wang, C. Xu, X. Tan, H. Peng, H. He, Org. Biomol. Chem. 10, 1680–1685 (2012)

    Article  CAS  Google Scholar 

  23. Q. Wu, J. Zhou, Z. Yao, F. Xu, Q. Shen, J. Org. Chem. 75, 7498–7501 (2010)

    Article  CAS  Google Scholar 

  24. W. Goldeman, M. Soroka, Synthesis 3019–3024 (2006)

  25. J.P. Abell, H. Yamamoto, J. Am. Chem. Soc. 130, 10521–10523 (2008)

    Article  CAS  Google Scholar 

  26. F. Jahani, B. Zamenian, S. Khaksar, M. Taibakhsh, Synthesis 3315–3318 (2010)

  27. S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 128, 7442–7443 (2006)

    Article  CAS  Google Scholar 

  28. Z. Zhao, W. Xue, X. gao, G. Tang, Y. Zhao, Chem. Asian J. 8, 713–716 (2013)

  29. A.R. Sardarian, B. Kaboudin, Synth. Commun. 27, 543–551 (1997)

    Article  CAS  Google Scholar 

  30. B. Kaboudin, L. Malekzadeh, Synlett 2807–2810 (2011)

  31. B. Kaboudin, F. Saadati, T. Yokomatsu, Tetrahedron Lett. 50, 1450–1452 (2009)

    Article  CAS  Google Scholar 

  32. B. Kaboudin, F. Saadati, T. Yokomatsu, Synlett 1837–1840 (2010)

  33. B. Kaboudin, S. Alaie, T. Yokomatsu, Tetrahedron Asymmetry 22, 1816–1831 (2011)

  34. B. Kaboudin, T. Haruki, T. Yamagishi, T. Yokomatsu, Synthesis 3226–3232 (2007)

  35. F. Texier-Bullet; A. Foucaud, Synthesis 916 (1982)

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Acknowledgments

The authors gratefully acknowledge the support by the Institute for Advanced Studies in Basic Sciences (IASBS). Thanks are also given to Professor Behzad Haghighi for the atomic absorption analysis of the catalyst.

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Correspondence to Babak Kaboudin.

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Kaboudin, B., Kazemi, F. & Habibi, F. MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates. J IRAN CHEM SOC 12, 469–475 (2015). https://doi.org/10.1007/s13738-014-0504-9

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  • DOI: https://doi.org/10.1007/s13738-014-0504-9

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