Skip to main content
Log in

Mild and efficient silylation of alcohols under ambient and solvent-free conditions with phosphorus pentoxide supported on alumina (P2O5/Al2O3) as catalyst

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

Abstract

P2O5/Al2O3, an easily handled recyclable catalyst, has been used in an eco-friendly and mild procedure for trimethylsilyl protection of alcohols by use of hexamethyldisilazane. Solvent-free, ambient reaction conditions, easy work-up, short reaction times, excellent yields and reusability of the catalyst are noticeable features of this method.

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
Scheme 2

Similar content being viewed by others

References

  1. P.G.M. Wuts, T.W. Greene, Greene’s protective groups in organic synthesis, 4th edn. (Wiley–Interscience, New York, 2007)

    Google Scholar 

  2. G. Van Look, G. Simchen, J. Heberle (eds.), Silylation agents (Fluka, Buchs, Switzerland) (1995)

  3. P.J. Kocienski, Protecting groups (Georg Thieme Verlag, Stuttgart, 2005)

    Google Scholar 

  4. C.A. Bruynes, T.K. Jurriens, J. Org. Chem. 47, 3966 (1982)

    Article  CAS  Google Scholar 

  5. B.P. Bandgar, P.P. Wadgaonkar, Synth. Commun. 27, 2069 (1997)

    Article  CAS  Google Scholar 

  6. H. Firouzabadi, N. Iranpoor, K. Amani, F. Nowrouzi, J. Chem. Soc. Perkin 1 23, 2601 (2002)

    Article  Google Scholar 

  7. Z.H. Zhang, T.S. Li, F. Yang, C.G. Fu, Synth. Commun. 28, 3105 (1998)

    Article  CAS  Google Scholar 

  8. B. Akhlaghinia, S. Tavakoli, Synthesis, 1775 (2005)

  9. N. Azizi, R. Yousefi, M.R. Saidi, J. Organomet. Chem. 691, 817 (2006)

    Article  CAS  Google Scholar 

  10. D. Zareyee, B. Karimi, Tetrahedron Lett. 48, 1277 (2007)

    Article  CAS  Google Scholar 

  11. H. Firouzabadi, N. Iranpoor, S. Sobhani, S. Gassamipour, J. Organomet. Chem. 689, 3197 (2004)

    Article  CAS  Google Scholar 

  12. P. Villabrille, G. Romanelli, N. Quaranta, P. Vázquez, Appl. Catal. B 96, 379 (2010)

    Article  CAS  Google Scholar 

  13. H. Firouzabadi, N. Iranpoor, A.A. Jafari, M.R. Jafari, J. Organomet. Chem. 693, 2711 (2008)

    Article  CAS  Google Scholar 

  14. H.R. Shaterian, F. Shahrekipoor, M. Ghashang, J. Mol. Catal. A Chem. 272, 142 (2007)

    Article  CAS  Google Scholar 

  15. M.M. Mojtahedi, M.S. Abaee, M. Eghtedari, Appl. Organometal. Chem. 22, 529 (2008)

    Article  CAS  Google Scholar 

  16. A. Khazaei, M.A. Zolfigol, Z. Tanbakouchian, M. Shiri, K. Niknam, J. Saien, Catal. Commun. 8, 917 (2007)

    Article  CAS  Google Scholar 

  17. H. Firouzabadi, N. Iranpoor, S. Farahi, J. Organomet. Chem. 694, 3923 (2009)

    Article  CAS  Google Scholar 

  18. F. Shirini, N. Ghaffari Khaligh, J. Iran. Chem. Soc. 9, 495 (2012)

    Article  CAS  Google Scholar 

  19. F. Rajabi, R. Luque, J.C. Serrano-Ruiz, Chem. Biodivers. 9, 1823 (2012)

    Article  CAS  Google Scholar 

  20. S.T. Kadam, S.S. Kim, Green Chem. 12, 94 (2010)

    Article  CAS  Google Scholar 

  21. A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, S. Zahmatkesh, J. Mol. Catal. A Chem. 301, 39 (2009)

    Article  CAS  Google Scholar 

  22. A.V. Narsaiah, J. Organomet. Chem. 692, 3614 (2007)

    Article  CAS  Google Scholar 

  23. N. Azizi, M.R. Saidi, Organometallics 23, 1457 (2004)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the University of Sistan and Baluchestan Research Council for partial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hamid Reza Shaterian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaterian, H.R., Fahimi, N. & Azizi, K. Mild and efficient silylation of alcohols under ambient and solvent-free conditions with phosphorus pentoxide supported on alumina (P2O5/Al2O3) as catalyst. Res Chem Intermed 41, 947–954 (2015). https://doi.org/10.1007/s11164-013-1247-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1247-4

Keywords

Navigation