Skip to main content
Log in

Synthesis and characterization of novel silica coated magnetic nanoparticles with tags of β-cyclodextrin: application as an eco-friendly and chiral micro-vessel catalyst in the enantioselective reduction of ketones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, we report the synthesis of a novel, green and recoverable organic–inorganic magnetic nanocomposite by grafting β-cyclodextrin on the surface of a silica-coated magnetic nanoparticle, Fe3O4@SiO2/Pr-β-CD. FT-IR spectroscopy, transmission electron microscopy, CHN analysis, thermogravimetric analysis, vibrating sample magnetometer and X-ray diffraction analyses confirmed its structure. The magnetic core–shell structured modified silica microsphere has been successfully used as a chiral micro-vessel catalyst for the enantioselective reduction of ketones by NaBH4. The described catalyst was regenerated and reused without any significant changes in the yield and enantiomeric excess.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Fig. 7

Similar content being viewed by others

References

  1. Z. Tai, M.A. Isaacs, C.M.A. Parlett, A.F. Lee, K. Wilson, Catal. Commun. 92, 56 (2017)

    Article  CAS  Google Scholar 

  2. P. Rezaee, J. Davarpanah, Res. Chem. Intermed. 42, 6815 (2016)

    Article  CAS  Google Scholar 

  3. N. Sounderya, Y. Zhang, Recent Pat. Biomed. Eng. 1, 34 (2008)

    Article  CAS  Google Scholar 

  4. S. Sadjadi, M. Malmir, M.M. Heravi, RSC Adv. 7, 36807 (2017)

    Article  CAS  Google Scholar 

  5. S. Xu, H. Lu, L. Chen, X. Wang, RSC Adv. 4, 45266 (2014)

    Article  CAS  Google Scholar 

  6. W. Lu, J. Li, Y. Sheng, X. Zhang, J. You, L. Chen, J. Colloid Interface Sci. 505, 1134 (2017)

    Article  CAS  Google Scholar 

  7. S. Xu, H. Lu, X. Zheng, L. Chen, J. Mater. Chem. C 1, 4406 (2013)

    Article  CAS  Google Scholar 

  8. H. Cao, J. He, L. Deng, X. Gao, Appl. Surf. Sci. 255, 7974 (2009)

    Article  CAS  Google Scholar 

  9. Y. Wang, H. Chen, Y. Xiao, C.H. Ng, T.S. Oh, T.T.Y. Tan, Nat. Protoc. 6, 935 (2011)

    Article  CAS  Google Scholar 

  10. F. Bellia, D.L. Mendola, C. Pedone, Chem. Soc. 38, 2756 (2009)

    Article  CAS  Google Scholar 

  11. M. Wills, Angew. Chem. Int. Edit. 47, 4264 (2008)

    Article  CAS  Google Scholar 

  12. E.B. Kurbanoglu, K. Zilbeyaz, N.I. Kurbanoglu, Tetrahedron 18, 2332 (2007)

    Article  CAS  Google Scholar 

  13. F. Degerbeck, B. Fransson, L. Grehn, U.J. Ragnarsson, J. Chem. Soc. Perkin Trans. 1, 245 (1992)

    Article  Google Scholar 

  14. E.J. Corey, S. Wei-guo, Tetrahedron Lett. 31, 3833 (1990)

    Article  CAS  Google Scholar 

  15. J. Szetjli, Chem. Rev. 98, 1743 (1998)

    Article  Google Scholar 

  16. E.D. Mark, E.B. Marcus, Nat. Rev. Drug. Discov. 3, 1023 (2004)

    Article  Google Scholar 

  17. K.D. Kim, S.S. Kim, Y.H. Choa, H.T. Kim, J. Ind. Eng. Chem. 13, 1137 (2007)

    CAS  Google Scholar 

  18. H.Y. Deng, C.C. Wang, J.H. Hu, W.L. Yang, S.K. Fu, Colloids Surf. A 262, 87 (2005)

    Article  CAS  Google Scholar 

  19. A.R. Kiasat, S. Nazari, J. Incl. Phenom. Macrocycl. Chem. 77, 429 (2013)

    Article  CAS  Google Scholar 

  20. A.Z.M. Badruddoza, K. Hidajat, M.S. Uddin, J. Colloid Interface Sci. 346, 337 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the Research Council of Shahid Chamran University for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mina Jafari Nasab.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jafari Nasab, M., Kiasat, A.R. Synthesis and characterization of novel silica coated magnetic nanoparticles with tags of β-cyclodextrin: application as an eco-friendly and chiral micro-vessel catalyst in the enantioselective reduction of ketones. Res Chem Intermed 44, 2719–2728 (2018). https://doi.org/10.1007/s11164-018-3256-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3256-9

Keywords

Navigation