Advertisement

Dendrimer-encapsulated copper(II) immobilized on Fe3O4@SiO2 NPs: a robust recoverable catalyst for click synthesis of 1,2,3-triazole derivatives in water under mild conditions

  • Ali Reza Sardarian
  • Fattah Mohammadi
  • Mohsen Esmaeilpour
Article
  • 12 Downloads

Abstract

In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases. This present methodology is a clean, and environmentally friendly approach that offers many advantages including excellent yields, operational simplicity, short reaction time, and absence of any tedious workup or purification. Moreover, of interesting features are the stability of the catalyst toward leaching and the possibility of catalyst recycling without any significant loss of activity.

Graphical abstract

In this paper, we have introduced Fe3O4@SiO2-dendrimer-encapsulated Cu(II) as a heterogeneous reusable catalyst for Cu-catalyzed azide-alkyne cycloaddition reaction (CuAAC) in good to excellent yields at ambient temperature in water without requiring ligands, reducing agents and bases.

Keywords

Click reaction Multicomponent reaction Triazole Water Magnetic dendrimer catalyst 

Notes

Acknowledgements

The authors are grateful to the council of the Iran National Science Foundation and Shiraz University for their partially financial support to undertake this work.

References

  1. 1.
    C. Xu, K. Xu, H. Gu, R. Zheng, H. Liu, X. Zhang, Z. Guo, B. Xu, J. Am. Chem. Soc. 126, 9938 (2004)CrossRefGoogle Scholar
  2. 2.
    X. Li, X.H. Zhu, Y. Fang, H.L. Yang, X. Zhou, W. Chen, L. Jiao, H. Huo, R. Li, Mater. Chem A. 2, 10485 (2014)CrossRefGoogle Scholar
  3. 3.
    M. Esmaeilpour, A. Sardarian, J. Javidi, Catal. Sci. Technol. 6, 4005 (2016)CrossRefGoogle Scholar
  4. 4.
    Z.L. Lu, W.Q. Zou, L.Y. Lv, X.C. Liu, S.D. Li, J.M. Zhu, F.M. Zhang, Y.W. Du, J. Phys. Chem. B. 110, 23817 (2006)CrossRefGoogle Scholar
  5. 5.
    M. Esmaeilpour, J. Javidi, D. Divar, J. Magn. Magn. Mater. 423, 232 (2017)CrossRefGoogle Scholar
  6. 6.
    Q.A. Pankhurst, J. Connolly, S.K. Jones, J. Dobson, J. Phys. D Appl. Phys. 36, R167 (2003)CrossRefGoogle Scholar
  7. 7.
    M. Esmaeilpour, A.R. Sardarian, A. Jarrahpour, E. Ebrahimi, J. Javidi, RSC Adv. 6, 43376 (2016)CrossRefGoogle Scholar
  8. 8.
    T. Sen, I.J. Bruce, Microporous Mesoporous Mater. 120, 246 (2009)CrossRefGoogle Scholar
  9. 9.
    J. Javidi, M. Esmaeilpour, M. Rajabnia Khansari, RSC Adv. 5, 73268 (2015)CrossRefGoogle Scholar
  10. 10.
    A.H. Lu, E.L. Sahabas, F. Schuth, Angew. Chem. Int. Ed. 46, 1222 (2007)CrossRefGoogle Scholar
  11. 11.
    M. Esmaeilpour, J. Javidi, F. Dehghani, S. Zahmatkesh, Res. Chem. Intermed. 43, 163 (2017)CrossRefGoogle Scholar
  12. 12.
    A. Yin, C. Wen, W. Dai, K. Fan, Appl. Surf. Sci. 257, 5844 (2011)CrossRefGoogle Scholar
  13. 13.
    G. Toskas, C. Cherif, R.D. Hund, E. Laourine, A. Fahmi, B. Mahltig, ACS Appl. Mater. Interfaces 3, 3673 (2011)CrossRefGoogle Scholar
  14. 14.
    R.B. Nasir Baig, R.S. Varma, Chem. Commun. 49, 752 (2013)CrossRefGoogle Scholar
  15. 15.
    H.J. Lee, H. Jeon, W.S. Lee, J. Phys. Chem. C 116, 9180 (2012)CrossRefGoogle Scholar
  16. 16.
    M. Esmaeilpour, J. Javidi, S. Zahmatkesh, N. Fahimi, Monatshefte Chem. 148, 947 (2017)CrossRefGoogle Scholar
  17. 17.
    M. Esmaeilpour, J. Javidi, M. Mokhtari Abarghoui, F. Nowroozi Dodeji, J. Iran. Chem. Soc. 11, 499 (2014)CrossRefGoogle Scholar
  18. 18.
    G.R. Newkome, C. Shreiner, Chem. Rev. 110, 6338 (2010)CrossRefGoogle Scholar
  19. 19.
    H. Tokuhisa, M. Kanesato, Langmuir 21, 9728 (2005)CrossRefGoogle Scholar
  20. 20.
    M. Esmaeilpour, J. Javidi, F. Dehghani, J. Iran. Chem. Soc. 13, 695 (2016)CrossRefGoogle Scholar
  21. 21.
    R.M. Crooks, M. Zhao, L. Sun, V. Chechik, L.K. Yeung, Acc. Chem. Res. 34, 181 (2001)CrossRefGoogle Scholar
  22. 22.
    R.W.J. Scott, O.M. Wilson, R.M. Crooks, J. Phys. Chem. B 109, 692 (2005)CrossRefGoogle Scholar
  23. 23.
    P. Maity, S. Yamazoc, T. Tsukuda, ACS Catal. 3, 182 (2013)CrossRefGoogle Scholar
  24. 24.
    S. Pan, S. Yan, T. Osako, Y. Uozumi, ACS Sustain. Chem. Eng. 5, 10722 (2017)CrossRefGoogle Scholar
  25. 25.
    S. Chandra, G. Noronha, S. Dietrich, H. Lang, D. Bahadur, J. Magn. Magn. Mater. 380, 7 (2015)CrossRefGoogle Scholar
  26. 26.
    O.A. Attanasi, G. Favi, A. Geronikaki, F. Mantellini, G. Moscatelli, A. Paparisva, Org. Lett. 15, 2624 (2013)CrossRefGoogle Scholar
  27. 27.
    B. Schulze, U.S. Schubert, Chem. Soc. Rev. 43, 2523 (2014)CrossRefGoogle Scholar
  28. 28.
    H.L. Cui, Y.C. Chen, Chem. Commun. 4479 (2009)Google Scholar
  29. 29.
    J.F. Lutz, Angew. Chem. Int. Ed. 47, 2182 (2008)CrossRefGoogle Scholar
  30. 30.
    P. Thirumurugan, D. Matosiuk, K. Jozwiak, Chem. Rev. 113, 4905 (2013)CrossRefGoogle Scholar
  31. 31.
    G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, A.A. Genazzani, Med. Res. Rev. 28, 278 (2008)CrossRefGoogle Scholar
  32. 32.
    T. Lee, M. Cho, S.Y. Ko, H.J. Youn, D.J. Baek, W.J. Cho, C.Y. Kang, S. Kim, J. Med. Chem. 50, 585 (2007)CrossRefGoogle Scholar
  33. 33.
    R. Huisgen, Pure Appl. Chem. 61, 613 (1989)CrossRefGoogle Scholar
  34. 34.
    R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, ed. by A. Padwa (Wiley, New York, 1984)Google Scholar
  35. 35.
    C.W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 67, 3057 (2002)CrossRefGoogle Scholar
  36. 36.
    V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. 41, 2596 (2002)CrossRefGoogle Scholar
  37. 37.
    J.M. Fraile, J.I. Garcia, J.A. Mayoral, M. Roldan, Org. Lett. 9, 731 (2007)CrossRefGoogle Scholar
  38. 38.
    N. Candelon, D. Lastecoueres, A.K. Diallo, J.R. Aranzaes, D. Astruc, J.M. Vincent, Chem. Commun. 741 (2008)Google Scholar
  39. 39.
    B.J. Borah, D. Dutta, P.P. Saikia, N.Ch. Baruab, D.K. Dutta, Green Chem. 13, 3453 (2011)CrossRefGoogle Scholar
  40. 40.
    T.R. Chan, V.V. Fokin, QSAR Comb. Sci. 26, 1274 (2007)CrossRefGoogle Scholar
  41. 41.
    K. Martina, S.E.S. Leonhardt, B. Ondruschka, M. Carini, A. Binello, G. Cravotto, J. Mol. Catal. A Chem. 334, 60 (2011)CrossRefGoogle Scholar
  42. 42.
    F. Alonso, Y. Moglie, G. Radivoy, M. Yus, Adv. Synth. Catal. 352, 3208 (2010)CrossRefGoogle Scholar
  43. 43.
    C.T. Lee, S. Huang, B.H. Lipshutz, Adv. Synth. Catal. 351, 3139 (2009)CrossRefGoogle Scholar
  44. 44.
    T. Shamim, S. Paul, Catal. Lett. 136, 260 (2010)CrossRefGoogle Scholar
  45. 45.
    T. Miao, L. Wang, Synthesis 2008, 363 (2008)CrossRefGoogle Scholar
  46. 46.
    S. Chassing, A.S.S. Sido, A. Alix, M. Kumarraja, P. Pale, J. Sommer, Chem. Eur. J. 14, 6713 (2008)CrossRefGoogle Scholar
  47. 47.
    K. Yamaguchi, T. Oishi, T. Katayama, N. Mizuno, Chem. Eur. J. 15, 10464 (2009)CrossRefGoogle Scholar
  48. 48.
    K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 47, 2407 (2008)CrossRefGoogle Scholar
  49. 49.
    K. Kamata, Y. Nakagawa, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 130, 15304 (2008)CrossRefGoogle Scholar
  50. 50.
    Y. Wang, J. Liu, C. Xia, Adv. Synth. Catal. 353, 1534 (2011)CrossRefGoogle Scholar
  51. 51.
    Y. Masuyama, K. Yoshikawa, N. Suzuki, K. Hara, A. Fukuoka, Tetrahedron Lett. 52, 6916 (2011)CrossRefGoogle Scholar
  52. 52.
    K. Namitharan, M. Kumarraja, K. Pitchumani, Chem. Eur. J. 15, 2755 (2009)CrossRefGoogle Scholar
  53. 53.
    M. Esmaeilpour, J. Javidi, M. Zandi, New J. Chem. 39, 3388 (2015)CrossRefGoogle Scholar
  54. 54.
    M. Esmaeilpour, J. Javidi, S. Zahmatkesh, Appl. Organomet. Chem. 30, 897 (2016)CrossRefGoogle Scholar
  55. 55.
    M. Esmaeilpour, J. Javidi, J. Chin. Chem. Soc. 62, 328 (2015)CrossRefGoogle Scholar
  56. 56.
    M. Esmaeilpour, A.R. Sardarian, H. Firouzabadi, Appl. Organomet. Chem. 32, e4300 (2018)CrossRefGoogle Scholar
  57. 57.
    J. Javidi, M. Esmaeilpour, Mater. Res. Bull. 73, 409 (2016)CrossRefGoogle Scholar
  58. 58.
    C. Zhang, B. Huang, Y. Chen, D.M. Cui, New J. Chem. 37, 2606 (2013)CrossRefGoogle Scholar
  59. 59.
    H. Sharghi, R. Khalifeh, M.M. Doroodmand, Adv. Synth. Catal. 351, 207 (2009)CrossRefGoogle Scholar
  60. 60.
    P. Appukkuttan, W. Dehaen, V.V. Fokin, E.V. Eycken, Org. Lett. 6, 4223 (2004)CrossRefGoogle Scholar
  61. 61.
    S. Nekkanti, K. Veeramani, S.S. Kumari, R. Tokala, N. Shankaraiah, ARC Adv. 6, 103556 (2016)Google Scholar
  62. 62.
    Z. Hasanpour, A. Maleki, M. Hosseini, L. Gorgannezhad, V. Nejadshafiee, A. Ramazani, I. Haririan, A. Shafiee, M. Khoobi, Turk. J. Chem. 41, 294 (2017)CrossRefGoogle Scholar
  63. 63.
    D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, B. Che, Green Chem. 12, 2120 (2010)CrossRefGoogle Scholar
  64. 64.
    F. Matloubi Moghaddam, S.E. Ayati, RSC Adv. 5, 3894 (2015)CrossRefGoogle Scholar
  65. 65.
    T.Y. Kim, A.B.S. Elliott, K.J. Shaffer, C.J. McAdam, K.C. Gordon, J.D. Crowley, Polyhedron 52, 1391 (2013)CrossRefGoogle Scholar
  66. 66.
    Z. Chen, Q. Yan, H. Yi, Z. Liu, A. Lie, Y. Zhang, Chem. Eur. J. 20, 1 (2014)CrossRefGoogle Scholar
  67. 67.
    C. Girard, E. Onen, M. Aufort, S. Beauviere, E. Samson, J. Herscovici, Org. Lett. 8, 1689 (2006)CrossRefGoogle Scholar
  68. 68.
    R. Jahanshahi, B. Akhlaghinia, RSC Adv. 6, 29210 (2016)CrossRefGoogle Scholar
  69. 69.
    M. Rivara, M.K. Patel, L. Amori, V. Zuliani, Bioorg. Med. Chem. Lett. 22, 6401 (2012)CrossRefGoogle Scholar
  70. 70.
    M. Nasrollahzadeh, S.M. Sajadi, Y. Mirzaei, J. Colloid Interface Sci. 468, 156 (2016)CrossRefGoogle Scholar
  71. 71.
    V. Bénéteau, A. Olmos, T. Boningari, J. Sommer, P. Pale, Tetrahedron Lett. 51, 3673 (2010)CrossRefGoogle Scholar
  72. 72.
    S. Hohloch, B. Sarkar, L. Nauton, F. Cisnetti, A. Gautier, Tetrahedron Lett. 54, 1808 (2013)CrossRefGoogle Scholar
  73. 73.
    A. Banan, A. Bayat, H. Valizadeh, Appl. Organomet. Chem. 31, e3604 (2016)CrossRefGoogle Scholar
  74. 74.
    B.S.P. Anil Kumar, K. Harsha Vardhan Reddy, B. Madhav, K. Ramesh, Y.V.D. Nageswar, Tetrahedron Lett. 53, 4595 (2012)CrossRefGoogle Scholar
  75. 75.
    L. Huang, W. Liu, J. Wu, Y. Fu, K. Wang, C. Huo, Z. Du, Tetrahedron Lett. 55, 2312 (2014)CrossRefGoogle Scholar
  76. 76.
    S. Mohammed, A.K. Padala, B.A. Dar, B. Singh, B. Sreedhar, R.A. Vishwakarma, S.B. Bharate, Tetrahedron 68, 8156 (2012)CrossRefGoogle Scholar
  77. 77.
    K. Takannabe, T. Uzawa, X. Wang, K. Maeda, M. Katayama, J. Kubata, A. Kudo, K. Domen, Dalton Trans. 10055 (2009)Google Scholar
  78. 78.
    F.-Z. Zhao, P.-H. Zeng, S.-F. Ji, X. Yang, C.-Y. Li, Acta Phys. Chim. Sin. 26, 3285 (2010)Google Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Chemistry, College of SciencesShiraz UniversityShirazIran

Personalised recommendations