Sulfonated polystyrene/montmorillonite nanocomposite as a new and efficient catalyst for the solvent-free Mannich reaction

Authors

1 Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 86145-311, Iran.

2 Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza, Isfahan, 86145-311, Iran. Razi Chemistry Research Center, Shahreza Branch, Islamic Azad University Shahreza, Isfahan, 86145-311, Iran

Abstract

Sulfonated polystyrene/montmorillonite nanocomposite (OMMT/PS-SO3H) was prepared and used as a novel, efficient and inexpensive heterogeneous acid catalyst in the one-pot reaction three-component Mannich reaction of ketones, aromatic aldehydes and amines under solvent-free conditions. The catalyst was characterized by XRD, SEM, TG, BET and FT-IR techniques. This method has advantages of high yield, moderate to excellent diasteroselectivity, mild condition, catalyst recyclability, and simple work-up procedure.

Keywords


  1. I. N. Rao, E. N. Prabhakaran, S. K.Das, J. Iqbal, J. Org. Chem. 68 (2003) 4079-4082.
  2. B. Trost, L. Terrell, J. Am. Chem. Soc. 125 (2003) 338-339.
  3. M.B. Gawande, R.V. Jayaram, Catal. Commun. 7 (2006) 931–935.
  4. H. Wu, Y. Shen, L.Y. Fan, Tetrahedron 63 (2007) 2404-2408.
  5. M.A. Bigdeli, F. Nemati G.H. Mahdavinia, Tetrahedron Lett. 48 (2007)  6801-6804.
  6. Y.G. Wang, Y.Y. Yang, W.G. Shou, Tetrahedron 62 (2006) 10079-10086.
  7. M. Wu, H.W. Jing, T. Change, Catal. Commun. 8 (2007) 2217-2221.
  8. T. Rosenau, A. Pottast, Tetrahedron 60 (2004) 301-306.
  9. B. List, P. Pojarliev, W.T. Biller, H. J. Martin, J. Am. Chem. Soc. 124 (2002) 827-833.
  10. G. Valero, A. Balaguer, A. Moyano, R. Rios, Tetrahedron Lett. 49 (2008) 6559-6562.
  11. V. Sukach, N. Golovach, V. Pirozhenko, E. Rosanov, M. Vovk, Tetrahedron 49 (2008) 761-765.
  12. H. Wu, X.M. Chen, Y. Wan, L. Ye, H.Q. Xin, H.H. Xu, C.H. Yue, L.I. Pang, R. Ma, D.Q. Shi, Tetrahedron Lett. 50 (2009) 1062-1065.
  13. (a) H. Xing, T. Wang, Zhou,Z., Y. Dai, J. Mol. Catal. A: Chem. 264 (2007) 53; (b) A.R. Hajipour, Y. Gayeb, N. Sheikhan, A.E. Ruoho, Tetrahedron Lett. 50 (2009) 5649-5651.; (c) F. Dong, F. Zhenghao, L. Zuliang, Catal. Commun. 10 (2009) 1267.
  14. R.I. Kureshy, S. Agrawal, S. Saravanan, N. Khan, H. Shah, S. Abdi, H. Bajaj, E. Suresh, Tetrahedron Lett. 51 (2010) 489-494.
  15. M. Kidwai, N. Mishra, V. Bansal, A. Kumar, S. Mozumdar, Tetrahedron Lett. 50 (2009) 1355-1359.
  16.  (a) M. Alexander, P. Duboi, Mater. Sci. Eng. 28(1-2) (2000)
    1-63; (b) D.M. Lincoln, R. Vai, Z.G. Wang, B.S. Hsiao, Polymer. 42 (2001) 1621-1631; (c) B. Leppoittevin, M. Alexander, M. Devalckkenaere, D. Kubies, Polymer. 43 (2002) 4017-4023; (d) P. Maiti, P.H. Nam, M. Okanotom, N. Hasegawi, A. Usuki, Macromolecules 35 (2002) 2042-2049.
  17. D. Homminga, B. Goderhs, H. Reyaers, G. Groeninckx, Polymer. 46 (2005) 11359-11365.
  18. C. Felice, S. Ye, D. Qu,. Ind. Eng. Chem. Res. 49  (2010) 1514-1519.
  19. D.C. Rodrìguez-Sarmiento, J.A. Pinzón-Bello, Appl. Clay Sci. 18 (2001) 173–181.
  20. F. Bergaya, G. Lagaly, Appl. Clay Sci. 19, (2001) 1–6.
  21. N. Carretta, V.Tricoli, F. Picchioni, J. Membr. Sci. 166 (2000) 180-189.
  22. Q. Guo, P.N. Pintauro, H. Tang, S. O’Connor, J. Membr. Sci. 154 (1999) 175-181.
  23. F. Wang, M. Hickner, Y.S. Kim, T.A. Zawodzinski, J.E. McGrath, J. Membr. Sci. 197 (2002) 231-242.
  24. C. Manea, M. Mulder, J. Membr. Sci. 206 (2002) 443-53.
  25. (a) A.R. Massah, M. Dabagh, M. Afshar, A. Momeni, H. Aliyan, H. Javaherian Naghash, Turk. J. Chem. 31 (2007) 611-616; (b) R.J. Kalbasi, M. Ghiaci, A.R. Massah, Appl. Catal. A: Gen. 353 (2009) 1-6; (c) R.J. Kalbasi, Massah, A.R., Z. Barkhordari, Bul. Korean. Chem. Soc. 31 (2010) 2361-2367; (d) R.J. Kalbasi, A. Abbaspourrad A.R. Massah, F. Zamani, Chin. J. Chem. 28 (2010) 273-284.
  26. (a) A.R. Massah, B. Asadi, M. Hoseinpour, A. Molseghi, R.J. Kalbasi, H. Javaherian Naghash, Tetrahedron 65 (2009) 7696-7705; (b) A.R. Massah, D. Azadi, H. Aliyan, A.R. Momeni, F. Kazemi, Monatsh. Fur. Chem. 139 (2008) 233-238; (c) A.R. Massah, M. Mosharafian, A.R. Momeni, H. Aliyan, H. Javaherian Naghash, M. Adibnejad, Synth. Commun. 37 (2007) 1807-1815; (d) F. Kazemi, A.R. Massah, H. Javaherian Naghash, Tetrahedron 63 (2007) 5083-5087.
  27. R.J. Kalbasi, M. Kolahdoozan, A.R. Massah, K. Shahabian, Bull. Korean. Chem. Soc. 31 (2010) 2618-2626.
  28. A. Ganguly, A.K. Bhowmick, Nanoscale Res. Lett. (2008) 36-44.
  29. Y.Y. Yang, Y.G. Wang, Tetrahedron 62 (2006) 10079-10086.