Skip to main content
Log in

Direct aerobic oxidation of primary alcohols to methyl esters catalyzed by a heterogeneous gold catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Methyl esters can be produced in high yields by oxiding methanolic solutions of primary alcohols with dioxygen over a heterogeneous gold catalyst. The versatility of this new methodology is demonstrated by the fact that alkylic, benzylic and allylic alcohols, as well as alcohols containing an amine functionality are oxidized in good to excellent yields.

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.

Figure 1.
Figure 2.
Figure 3.
Figure 4.
Figure 5.

Similar content being viewed by others

References

  1. ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. (2000) Science 287:1636

    Article  CAS  Google Scholar 

  2. Mori K., Hara T., Mizugaki T., Ebitani K., Kaneda K. (2004) J. Am Chem. Soc. 126:10657

    Article  CAS  Google Scholar 

  3. Ebitani K., Motokura K., Muzugaki K., Kaneda K. (2005) Angew. Chem Int. Ed. 44:3423

    Article  CAS  Google Scholar 

  4. Mallat T., Baiker A. (2004) Chem. Rev. 104:3037

    Article  CAS  Google Scholar 

  5. Hutchings G.J., Haruta M. (2005) Appl. Catal. A. 291:2

    Article  CAS  Google Scholar 

  6. Hutchings G.J. (2005) Catal. Today 100:55

    Article  CAS  Google Scholar 

  7. Bond G.C., Louis C., Thompson D.T. (2006) Catalysis by Gold. Imperial College Press, London

    Google Scholar 

  8. Thompson D.T. (2006) Top. Catal. 38:231

    Article  CAS  Google Scholar 

  9. Haruta M., Kobayashi T., Sano H., Yamada N. (1987) Chem. Lett. 4:405

    Article  Google Scholar 

  10. Haruta M., Yamada N., Kobayashi T., Iilima S. (1989) J. Catal. 115:301

    Article  CAS  Google Scholar 

  11. Hutchings G.J. (1985) J. Catal. 96:292

    Article  CAS  Google Scholar 

  12. Prati L., Rossi M. (1998) J. Catal. 176:552

    Article  CAS  Google Scholar 

  13. Bianchi C., Porta F., Prati L., Rossi M. (2000) Top. Catal. 13:231

    Article  CAS  Google Scholar 

  14. S. Carrettin, P.McMorn, P. Johnston, K. Griffin, G.J Hutchings, Chem. Commun. (2002) 696

  15. Abad A., Almela C., Corma A., Garcia H. (2006) Tetrahedron 62 :6666

    Article  CAS  Google Scholar 

  16. Enache D.I., Knight D.W., Hutchings G.J. (2005) Catal. Lett. 103:43

    Article  CAS  Google Scholar 

  17. Christensen C.H., Jørgensen B., Rass-Hansen J., Egeblad K., Madsen R., Klitgaard S.K., Hansen S.M., Hansen M.R., Andersen H.C., Riisager A. (2006) Angew. Chem. Int. Ed. 45:4648

    Article  CAS  Google Scholar 

  18. Lopez N., Nørskov J.K. (2002) J. Am. Chem. Soc. 124:11262

    Article  CAS  Google Scholar 

  19. Valden M., Lai X., Goodmann D.W. (1998) Science 281:1647

    Article  CAS  Google Scholar 

  20. Mori N., Togo H. (2005) Tetrahedron 61:5915

    Article  CAS  Google Scholar 

  21. Hiegel G.A., Gilley C.B. (2003) Synth. Commun. 33:2003

    Article  CAS  Google Scholar 

  22. Karade N.N., Huple D.B. (2005) Synlett 13:2039

    Article  CAS  Google Scholar 

  23. Milocanovic J.N., Vasojevic M., Gojkovic S. (1991) J. Chem. Soc., Perkin Trans. 2:1231

    Google Scholar 

  24. McDonald C.E., Nice L.E., Nestor N.B. (1993) Tetrahedron Lett. 34:2744

    Article  Google Scholar 

  25. Y. Hiroshi, K. Ariyoshi, T. Hayashi, PCT Int. Patent Appl. WO 2004050600 (2004)

  26. Hayashi T., Inagaki T., Itayama N., Baba H. (2006) Catal. Today 117:210

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The Center for Sustainable and Green Chemistry is sponsored by the Danish National Research Foundation.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Claus H. Christensen.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nielsen, I.S., Taarning, E., Egeblad, K. et al. Direct aerobic oxidation of primary alcohols to methyl esters catalyzed by a heterogeneous gold catalyst. Catal Lett 116, 35–40 (2007). https://doi.org/10.1007/s10562-007-9086-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-007-9086-9

Keywords

Navigation