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Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite

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Abstract

An efficient protocol for the nitration of aromatic compounds in the presence of a catalytic amount of sulfuric acid-functionalized silica-based magnetic core/shell nanocomposite was reported. The designed products were obtained in high yields in relatively short reaction times at room temperature under solvent-free conditions. The nanocatalyst was simply recovered from the reaction mixture by using an external magnet and efficiently reused for several times. The characterization of particle size, morphology and elemental analysis of the nanocatalyst were provided by scanning electron microscopy, transmission electron microscopy and energy-dispersive X-ray spectroscopy analyses, respectively.

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References

  1. K. Schofield, Aromatic Nitration (University Press, Cambridge, 1980)

    Google Scholar 

  2. G.A. Olah, R. Malhotra, S.C. Narang, Nitration: Methods and Mechanisms (VCH, New York, 1989)

    Google Scholar 

  3. M.A. Zolfigol, E. Madrakian, E. Ghaemi, Molecules 7, 734 (2002)

    Article  CAS  Google Scholar 

  4. A. Khalafi-Nezhad, A. Parhami, M.N. Soltani Rad, M.A. Zolfigol, A. Zare, Tetrahedron Lett. 48, 5219 (2007)

    Article  CAS  Google Scholar 

  5. P. Salehi, M.A. Zolfigol, F. Shirini, M. Baghbanzadeh, Curr. Org. Chem. 10, 2171 (2006)

    Article  CAS  Google Scholar 

  6. M.A. Zolfigol, B.F. Mirjalili, A. Bamoniri, M. Zarchi, A. Karimi, A. Zarei, L. Khazdooz, J. Noei, Bull. Korean Chem. Soc. 25, 1414 (2004)

    Article  CAS  Google Scholar 

  7. M.A. Zolfigol, Tetrahedron 57, 9509 (2001)

    Article  CAS  Google Scholar 

  8. G. Chehardoli, M.A. Zolfigol, S.B. Azimi, E. Alizadeh, Chin. Chem. Lett. 22, 827 (2011)

    Article  CAS  Google Scholar 

  9. K. Smith, A. Musson, G.A. DeBoos, J. Org. Chem. 63, 8448 (1998)

    Article  CAS  Google Scholar 

  10. S.N. Nagy, J. Phys. Org. Chem. 7, 385 (1994)

    Article  CAS  Google Scholar 

  11. F. Nemati, H. Kiani, Chin. Chem. Lett. 21, 405 (2010)

    Article  Google Scholar 

  12. A. Ghorbani-Choghamarani, H. Goudarziafshar, M. Nikoorazm, Z. Naseri, Chin. Chem. Lett. 22, 1434 (2011)

    Google Scholar 

  13. F. Nemati, R. Saeedirad, Chin. Chem. Lett. 24, 370 (2013)

    Article  CAS  Google Scholar 

  14. J. Safari, Z.J. Zarnegar, Mol. Catal. A 379, 269 (2015)

    Article  Google Scholar 

  15. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, M. Saeedi, F.F. Bamoharram, Monatsh. Chem. 138, 449 (2017)

    Article  Google Scholar 

  16. A. Maleki, Tetrahedron 68, 7827 (2012)

    Article  CAS  Google Scholar 

  17. A. Maleki, Tetrahedron Lett. 54, 2055 (2013)

    Article  CAS  Google Scholar 

  18. A. Maleki, M. Kamalzare, Catal. Commun. 53, 67 (2014)

    Article  CAS  Google Scholar 

  19. A. Maleki, R. Paydar, RSC Adv. 5, 33177 (2015)

    Article  CAS  Google Scholar 

  20. A. Maleki, M. Aghaei, N. Ghamari, Chem. Lett. 44, 259 (2015)

    Article  CAS  Google Scholar 

  21. A. Maleki, Z. Alrezvani, S. Maleki, Catal. Commun. 69, 29 (2015)

    Article  CAS  Google Scholar 

  22. A. Maleki, H. Movahed, R. Paydar, RSC Adv. 6, 13657 (2016)

    Article  CAS  Google Scholar 

  23. A. Maleki, H. Movahed, P. Ravaghi, Carbohydr. Poly. 156, 259 (2017)

    Article  CAS  Google Scholar 

  24. V.S.P. Ganjala, ChKP Neeli, ChV Pramod, M. Khagga, K.S.R. Rao, D.R. Burri, Catal. Commun. 49, 82 (2014)

    Article  CAS  Google Scholar 

  25. A.R. Hajipour, A.E. Ruoho, Tetrahedron Lett. 46, 8307 (2005)

    Article  CAS  Google Scholar 

  26. N. Nowrouzi, M. Zareh Jonaghani, Tetrahedron Lett. 52, 5081 (2011)

    Article  CAS  Google Scholar 

  27. T.N. Parac-Vogt, K. Binnemans, Tetrahedron Lett. 45, 3137 (2004)

    Article  CAS  Google Scholar 

  28. Y. Yuan, J. Nie, Z. Zhang, S. Wang, Appl. Catal. A 295, 170 (2005)

    Article  CAS  Google Scholar 

  29. R.R. Yadav, R.A. Vishwakarma, S.B. Bharate, Tetrahedron Lett. 53, 5958 (2012)

    Article  CAS  Google Scholar 

  30. R.E. March, M.R. Weir, F.A. Londry, S. Catinella, P. Traldi, J.A. Stone, W.B. Jacobs, Can. J. Chem. 72, 966 (1994)

    Article  CAS  Google Scholar 

  31. J. Liu, J. Li, J. Ren, B. Zeng, Tetrahedron Lett. 55, 1581 (2014)

    Article  CAS  Google Scholar 

  32. K. Mandai, T. Korenaga, T. Ema, T. Sakai, M. Furutani, H. Hashimoto, J. Takada, Tetrahedron Lett. 53, 329 (2012)

    Article  CAS  Google Scholar 

  33. N. Nowrouzi, A.M. Mehranpour, E. Bashiri, Z. Shayan, Tetrahedron Lett. 53, 4841 (2012)

    Article  CAS  Google Scholar 

  34. G.L. Tolnai, B. Petho, P. Krall, Z. Novaka, Adv. Synth. Catal. 356, 125 (2014)

    Article  CAS  Google Scholar 

  35. Y. Zhao, V. Snieckus, Org. Lett. 16, 390 (2014)

    Article  CAS  Google Scholar 

  36. G.A. Molander, L.N. Cavalcanti, J. Org. Chem. 77, 4402 (2012)

    Article  CAS  Google Scholar 

  37. N. Nonoyama, K. Chiba, K. Hisatome, H. Suzuki, F.A. Shintani, Tetrahedron Lett. 40, 6923 (1999)

    Article  Google Scholar 

  38. W. Zhang, J. Zhang, S. Ren, Y. Liu, J. Org. Chem. 79, 11508 (2014)

    Article  CAS  Google Scholar 

  39. J.M. Poirier, C. Vottero, Tetrahedron 45, 1415 (1989)

    Article  CAS  Google Scholar 

  40. L.C. Raiford, J.C. Colbert, J. Am. Chem. Soc. 47, 1454 (1925)

    Article  CAS  Google Scholar 

  41. S. Mo, P. Huang, J. Xu, Org. Biomol. Chem. 12, 4192 (2014)

    Article  CAS  Google Scholar 

  42. A. Farrokhi, K. Ghodrati, I. Yavari, Catal. Commun. 63, 41 (2015)

    Article  CAS  Google Scholar 

  43. A. Oikawa, G. Kindaichi, Y. Shimotori, M. Okimoto, M. Hoshi, Tetrahedron 71, 1705 (2015)

    Article  CAS  Google Scholar 

  44. J. Bergman, P. Sand, Tetrahedron Lett. 1984, 25 (1957)

    Google Scholar 

  45. B.S. Samant, M.G. Sukhthankar, Bioorg. Med. Chem. Lett. 2011, 21 (1015)

    Google Scholar 

  46. J. Liu, J. Li, J. Ren, B.B. Zeng, Tetrahedron Lett. 55, 1581 (2014)

    Article  CAS  Google Scholar 

  47. B.B. Trunz, R. Jdrysiak, D. Tweats, R. Brun, M. Kaiser, J. Suwinski, E. Torreele, Eur. J. Med. Chem. 46, 1524 (2011)

    Article  CAS  Google Scholar 

  48. G.K. Rao, A. Kumar, S. Kumar, U.B. Dupare, A.K. Singh, Organometallics 32, 2452 (2013)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge the partial support from the Research Council of the Iran University of Science and Technology.

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Authors and Affiliations

  1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, 16846-13114, Tehran, Iran

    Ali Maleki, Morteza Aghaei & Reza Paydar

Authors
  1. Ali Maleki
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  2. Morteza Aghaei
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  3. Reza Paydar
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Correspondence to Ali Maleki.

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Maleki, A., Aghaei, M. & Paydar, R. Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite. J IRAN CHEM SOC 14, 485–490 (2017). https://doi.org/10.1007/s13738-016-0996-6

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  • DOI: https://doi.org/10.1007/s13738-016-0996-6

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