Skip to main content
Log in

Highly selective asymmetry transfer hydrogenation of prochiral acetophenone catalyzed by palladium–chitosan on silica

  • Published:
Catalysis Letters Aims and scope Submit manuscript

The chitosan–palladium catalyst supported on silica was prepared and used to catalyze an asymmetry transfer hydrogenation of prochiral acetophenone to alcohol with formate salts as a hydrogen donor at atmosphere. The results indicate that palladium coordinates with amino group in chitosan to form palladium–chitosan complex and its performance for an asymmetry transfer hydrogenation of acetophenone is affected greatly by the reaction temperature, hydrogen donor and solvent. For the hydrogenation of acetophenone over the palladium–chitosan–silica catalyst, the suitable solvent is ethanol and hydrogen donor is ammonium formate or sodium formate. Using ammonium formate as H-donor at atmosphere and 80 °C, an enantiomeric excess of R-1-phenylethanol reaches 68.9%.

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.

Similar content being viewed by others

References

  1. G.I.P. Daniëlle C.J.K. Paul L.S. Anthony (2000) J. Org. Chem. 65 3010

    Google Scholar 

  2. A. Baiker (1998) Curr. Opin. Solid State Mater. Sci. 3 86

    Google Scholar 

  3. W.K. Sang J.B. Sung H. Taeghwan (2001) Micropor. Mesopor. Mater. 523 44–45

    Google Scholar 

  4. H. Takeda K. Kadowaki (1985) Agric. Biol. Chem. 49 3151

    Google Scholar 

  5. M.Y. Yin G.L. Yuan Y.Q. Wu (1999) J. Mol. Catal. A: Chem. 147 93

    Google Scholar 

  6. J. Zhang C.G. Xia (2002) J. Mol. Catal. (China), 16 465

    Google Scholar 

  7. E. Piron M. Accomintti A. Domard (1997) Langmuir 13 1653

    Google Scholar 

  8. O. Takeshi O. Hirohito H. Shohei (1995) J. Am. Chem. Soc. 117 2675

    Google Scholar 

  9. C. Salazzo R. Halle T. Francois (2000) J. Organomet. Chem. 603 30

    Google Scholar 

  10. M. Tommo K. Yoshinori E. Kokki (1998) J. Org. Chem. 63 2378

    Google Scholar 

  11. R. Alice H. Domien T. Francois (2001) Tetra: Asy. 12 811

    Google Scholar 

  12. T. Nakano J. Ando Y. Jshii (1987) Tech. Rep. Kansai Univ. 29 69

    Google Scholar 

  13. S. Papp A. Szücs I. Dékány (2001) Appl. Clay. Sci. 19 155

    Google Scholar 

  14. A.K. Zharmagambetova E.E. Ergozhin Y.L. Sheludyakov S.G. Mukhamedzhanova I.A. Kurmanbayeva B.A. Selenova B.A. Utkelov (2001) J. Mol. Catal. A: Chem. 177 165

    Google Scholar 

  15. S. Kajagopal A.F. Spatola (1995) J. Org. Chem. 60 1347

    Google Scholar 

  16. G. Brieger T. Nestrick (1974) Chem. Rev. 74 567

    Google Scholar 

  17. R.A.W. Johnstone A.H. Wilby I.D. Entwistle (1985) Chem. Rev. 85 129

    Google Scholar 

  18. G. Cavinato L. Toniolo (1996) J. Mol. Catal A: Chem. 106 25

    Google Scholar 

  19. S. Rajagopal A.F. Spatola (1997) Appl. Catal. A: Gen. 152 69

    Google Scholar 

  20. J.B. Daniel B.T. Catherine E.C.P. Mano (1998) Tetra.: Asy. 9 2015

    Google Scholar 

  21. P.N. Rylander (1976) Catalytic Hydrogenation over Platinum Metals Academic Press New York

    Google Scholar 

  22. M.V. Rajashekharam I. Bergault P. Fouilloux D. Schweich H. Delmas R.V. Chaudhari (1999) Catal. Today 48 83

    Google Scholar 

  23. G. Cavinato L. Toniolo (1996) J. Mol. Catal. A: Chem. 106 25

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Quanzhong Lu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sun, Y., Guo, Y., Lu, Q. et al. Highly selective asymmetry transfer hydrogenation of prochiral acetophenone catalyzed by palladium–chitosan on silica. Catal Lett 100, 213–217 (2005). https://doi.org/10.1007/s10562-004-3458-1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-004-3458-1

Keywords:

Navigation