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Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions

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Abstract

A new catalyst has been prepared via immobilization of Cu(proline)2 complex onto the surface of magnetic graphene. The fabricated nanocatalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD) analysis, vibrating-sample magnetometry (VSM), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), inductively coupled plasma (ICP) techniques, and elemental analysis. Its catalytic performance was investigated in the aldol reaction using a mild and ecofriendly procedure. The synthesized nanocomposite, which contains Cu(II) center as Lewis acid, was found to be an efficient catalyst for asymmetric aldol reactions, affording corresponding aldol products in high yield and excellent enantiomeric excess (> 90 %). The examined catalyst was prepared from low-cost, easily available starting materials and can be readily isolated by magnetic decantation for recycling and reuse in consecutive reactions without significant loss of activity.

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References

  1. M.T. Crimmins, B.W. King, E.A. Tabet, K. Chaudhary, J. Org. Chem. 66, 894 (2001)

    Article  CAS  PubMed  Google Scholar 

  2. L. Li, L.W. Xu, Y.D. Ju, G.Q. Lai, Synth. Commun. 39, 764 (2009)

    Article  CAS  Google Scholar 

  3. J. Kofoed, T. Darbre, J.L. Reymond, Chem. Commun. 14, 1482 (2006)

    Article  CAS  Google Scholar 

  4. N. Yoshikawa, Y.M.A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 121, 4168 (1999)

    Article  CAS  Google Scholar 

  5. V. Sivamurugan, R.S. Kumar, M. Palanichamy, V. Murugesan, J. Heterocyclic Chem. 42, 969 (2005)

    Article  CAS  Google Scholar 

  6. B.M. Soares, A.M. Aguilar, E.R. Silva, M.D. Coutinho-Neto, I.W. Hamley, M. Reza, J. Ruokolainene, W.A. Alves, Phys. Chem. Chem. Phys. 19, 1181 (2017)

    Article  CAS  PubMed  Google Scholar 

  7. R. Greco, L. Caciolli, A. Zaghi, O. Pandoli, O. Bortolini, A. Cavazzini, C. De Risi, A. Massi, React. Chem. Eng. 1, 183 (2016)

    Article  CAS  Google Scholar 

  8. D.G. Crivoi, R.A. Mirandaa, E. Finocchio, J. Llorca, G. Ramis, J.E. Sueiras, A.M. Segarra, F. Medina, Appl. Catal. A 519, 116 (2016)

    Article  CAS  Google Scholar 

  9. Y. Wang, H. Shen, L. Zhou, F. Hu, S. Xie, L. Jiang, Catal. Sci. Technol. 6, 6739 (2016)

    Article  CAS  Google Scholar 

  10. Z. An, Y. Guo, L. Zhao, Z. Li, J. He, ACS Catal. 4, 2566 (2014)

    Article  CAS  Google Scholar 

  11. S.M. Islam, A.S. Roy, R.C. Dey, S. Paul, J. Mol. Catal. A Chem. 394, 66 (2014)

    Article  CAS  Google Scholar 

  12. A. Lu, T.P. Smart, T.H. Epps III, D.A. Longbottom, R.K. O’Reilly, Macromolecules 44, 7233 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. M. Lombardo, F. Pasi, S. Easwar, C. Trombini, Synlett 16, 2471 (2008)

    Article  CAS  Google Scholar 

  14. B. List, Tetrahedron 58, 5573 (2002)

    Article  CAS  Google Scholar 

  15. D.J. Eyckens, H.L. Brozinski, J.P. Delaney, L. Servinis, S. Naghashian, L.C. Henderson, Catal. Lett. 146, 212 (2016)

    Article  CAS  Google Scholar 

  16. S.H. Hosseini, A. Asadnia, J. Nanomater. 2012, 1 (2012)

    Article  CAS  Google Scholar 

  17. Y. Jiang, C. Guo, H. Xia, I. Mahmood, C. Liu, H. Liu, J. Mol. Catal. B 58, 103 (2009)

    Article  CAS  Google Scholar 

  18. X. Zheng, S. Luo, L. Zhang, J.P. Cheng, Green Chem. 1, 455 (2009)

    Article  CAS  Google Scholar 

  19. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  20. J.H. Lee, Y.M. Huh, Y.W. Jun, J.W. Seo, J.T. Jang, H.T. Song, S. Kim, E.J. Cho, H.G. Yoon, J.S. Suh, J. Cheon, Nat. Med. 13, 95 (2007)

    Article  CAS  Google Scholar 

  21. R.F. Majidi, N.S. Sanjani, F. Agend, Thin Solid Films 515, 368 (2006)

    Article  CAS  Google Scholar 

  22. L.G. Bach, M.R. Islam, J.T. Kim, S.Y. Seo, K.T. Lim, Appl. Surf. Sci. 258, 2959 (2012)

    Article  CAS  Google Scholar 

  23. M. Bagheri, M. Masteri-Farahani, M. Ghorbani, J. Magn. Magn. Mater. 327, 58 (2013)

    Article  CAS  Google Scholar 

  24. J. Chen, B. Yao, C. Li, G. Shi, Carbon 64, 225 (2013)

    Article  CAS  Google Scholar 

  25. S. Sheshmani, R. Amini, Carbohydr. Polym. 95, 348 (2013)

    Article  CAS  PubMed  Google Scholar 

  26. V. Georgakilas, M. Otyepka, A.B. Bourlinos, V. Chandra, N. Kim, K.C. Kemp, P. Hobza, R. Zboril, K.S. Kim, Chem. Rev. 112, 6156 (2012)

    Article  CAS  PubMed  Google Scholar 

  27. D.S. Su, S. Perathoner, G. Centi, Chem. Rev. 113, 5782 (2013)

    Article  CAS  PubMed  Google Scholar 

  28. M.J. Allen, V.C. Tung, R.B. Kaner, Chem. Rev. 110, 132 (2009)

    Article  CAS  Google Scholar 

  29. J. Guo, Y. Li, Sh Zhu, Zh Chen, Q. Liu, D. Zhang, W.J. Moon, D.M. Song, RSC Adv. 2, 1356 (2012)

    Article  CAS  Google Scholar 

  30. X. Yan, J. Chen, Q. Xue, P. Miele, Micropor. Mesopor. Mater. 135, 137 (2010)

    Article  CAS  Google Scholar 

  31. P. Xiong, G. Hu, Y. Fan, W. Zhang, J. Zhu, X. Wang, J. Power Sources 266, 384 (2014)

    Article  CAS  Google Scholar 

  32. T. Rakjumar, G.R. Rao, J. Chem. Sci. 120, 587 (2008)

    Article  Google Scholar 

  33. L.T.A. Sofia, A. Krishnan, M. Sankar, N.K. Kala Raj, P. Manikandan, P.R. Rajamohanan, T.G. Ajithkumar, J. Phys. Chem. C 113, 21114 (2009)

    Article  CAS  Google Scholar 

  34. Y. Zhang, Y. Zhao, C. Xia, J. Mol. Catal. A 306, 107 (2009)

    Article  CAS  Google Scholar 

  35. J. Dupont, R.F. de Souza, P.A.Z. Suarez, Chem. Rev. 102, 3667 (2002)

    Article  CAS  Google Scholar 

  36. P. Virtanen, T.O. Salmi, J.P. Mikkola, Top. Catal. 53, 1096 (2010)

    Article  CAS  Google Scholar 

  37. Y. Inomata, T. Takeuchi, T. Moriwaki, Inorg. Chim. Acta 68, 187 (1983)

    Article  CAS  Google Scholar 

  38. W. Stöber, A. Fink, J. Colloid Interface Sci. 26, 62 (1968)

    Article  Google Scholar 

  39. N. Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C.F. Barbas III, J. Am. Chem. Soc. 128, 734 (2006)

    Article  CAS  PubMed  Google Scholar 

  40. M. Sadiq, R. Aman, K. Saeed, M.S. Ahmad, M.A. Zia, Mod. Res. Catal. 4, 43 (2015)

    Article  CAS  Google Scholar 

  41. Y.C. Teo, P.P.F. Lee, Synth. Commun. 39, 3081 (2009)

    Article  CAS  Google Scholar 

  42. M. M. Heravi, S. Asadi, Tetrahedron: Asymmetry, 2012, 23, 1431

  43. B.M. Trost, C.S. Brindle, Chem. Soc. Rev. 39, 1600 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. A. Khalafi-Nezhad, E.S. Shahidzadeh, S. Sarikhani, F. Panahi, J. Mol. Catal. A Chem. 379, 1 (2013)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful for support of this work (grant no. 1395) provided by the Research Council of Shahid Chamran University of Ahvaz, Iran.

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  1. Chemistry Department, Shahid Chamran University of Ahvaz, Ahvaz, Iran

    M. Kooti, F. Kooshki & E. Nasiri

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  1. M. Kooti
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  2. F. Kooshki
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  3. E. Nasiri
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Correspondence to M. Kooti.

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Kooti, M., Kooshki, F. & Nasiri, E. Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions. Res Chem Intermed 45, 2641–2656 (2019). https://doi.org/10.1007/s11164-019-03755-x

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