Skip to main content
SpringerLink
Log in

Aerobic oxidation of alcohols using a novel combination of N-hydroxyphthalimide (NHPI) and CuBr

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

Abstract

A new catalytic system for oxidation of alcohols with oxygen by N-hydroxyphthalimide (NHPI) combined with CuBr has been developed. The reaction results showed that this catalytic system can effectively catalyze the oxidation of alcohols to the corresponding carboxylic acids or ketones. We obtained 100% selectivity for acetophenone at 94.2% conversion of phenylethanol at 75 °C for 20 h. A mechanism of oxidation of alcohols catalyzed by NHPI/CuBr was proposed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. R.A. Sheldon, J. Kochi, Metal catalyzed oxidations of organic compounds (Academic Press, New York, 1981)

    Google Scholar 

  2. M. Hudlick, Oxidation in organic chemistry (ACS Press, Washington, 1990)

    Google Scholar 

  3. R.A. Sheldon, I.C.W.E. Arends, A. Dijksman, Catal. Today 57, 157–166 (2000)

    Article  CAS  Google Scholar 

  4. J.R. Holum, J. Org. Chem. 26, 4814–4816 (1961)

    Article  CAS  Google Scholar 

  5. J.C. Collins, W.W. Hess, F.J. Frank, Tetrahedron Lett. 30, 3363–3366 (1968)

    Article  Google Scholar 

  6. E.J. Corey, J.W. Suggs, Tetrahedron Lett. 31, 2647–2650 (1975)

    Article  Google Scholar 

  7. R.J. Highet, W.C. Wildman, J. Am. Soc. Chem. 77, 4399–4401 (1955)

    Article  CAS  Google Scholar 

  8. D.G. Lee, U.A. Spitzer, J. Org. Chem. 35, 3589–3590 (1970)

    Article  CAS  Google Scholar 

  9. R.V. Stevens, K.T. Chapman, H.N. Weller, J. Org. Chem. 45, 2030–2032 (1980)

    Article  CAS  Google Scholar 

  10. F.M. Menger, C. Lee, J. Org. Chem. 44, 3446–3448 (1979)

    Article  CAS  Google Scholar 

  11. B.M. Trost, Science 254, 1471–1477 (1991)

    Article  CAS  Google Scholar 

  12. B.M. Trost, Angew Chem. Int. Ed. 34, 259–281 (1995)

    Article  CAS  Google Scholar 

  13. T. Iwahama, S. Sakaguchi, Y. Nishiyama, Y. Ishii, Tetrahedron Lett. 36, 6923–6926 (1995)

    CAS  Google Scholar 

  14. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, Y. Ishii, J. Org. Chem. 65, 6502–6507 (2000)

    Article  CAS  Google Scholar 

  15. F. Minisci, C. Punta, F. Recupero, F. Fontana, G.F. Pedulli, Chem. Commun. (7), 688–689 (2002)

  16. P.J. Figiel, J.M. Sobczak, New J. Chem. 31(9), 1668–1673 (2007)

    Article  CAS  Google Scholar 

  17. P.J. Figiel, J.M. Sobczak, J.J. Ziolkowski, Chem. Commun. (2), 244–245 (2004)

  18. P.J. Figiel, J.M. Sobczak, J. Catal. 263(1), 167–172 (2009)

    Article  CAS  Google Scholar 

  19. B. Orlinska, Tetrahedron Lett. 51(31), 4100–4102 (2010)

    Article  CAS  Google Scholar 

  20. Y. Aoki, N. Hirai, S. Sakaguchi, Y. Ishii, Tetrahedron 61, 10995–10999 (2005)

    Article  CAS  Google Scholar 

  21. M. Nechab, C. Einhorn, J. Einhorn, Chem. Commun. (13), 1500–1501 (2004)

    Google Scholar 

  22. N. Koshino, B. Saha, J.H. Espenson, J. Org. Chem. 68(24), 9364–9370 (2003)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20643006), the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry and the National Basic Research Program of China (2009CB623505).

Author information

Authors and Affiliations

  1. School of Chemical & Material, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Gang Yang & Xiaoli Dong

  2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, People’s Republic of China

    Gang Yang, Lianyue Wang, Jun Li, Yi Zhang, Ying Lv & Shuang Gao

  3. Graduate School of the Chinese Academy of Sciences, Beijing, 100039, People’s Republic of China

    Lianyue Wang

Authors
  1. Gang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lianyue Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jun Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiaoli Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ying Lv
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Shuang Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shuang Gao.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, G., Wang, L., Li, J. et al. Aerobic oxidation of alcohols using a novel combination of N-hydroxyphthalimide (NHPI) and CuBr. Res Chem Intermed 38, 775–783 (2012). https://doi.org/10.1007/s11164-011-0416-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-011-0416-6

Keywords

Search

Navigation