Skip to main content
Log in

Ruthenium(II)-catalyzed transfer hydrogenation of aldehydes with new water-soluble monotosylated ethylenediamines as ligands

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

Abstract

New water-soluble monotosylated ethylenediamines containing quaternary ammonium groups were conveniently synthesized from ethylenediamine. The ruthenium catalysts prepared in situ from ruthenium complex [RuCl2(p-cymene)]2 and water-soluble monotosylated ethylenediamine ligands were used in transfer hydrogenation of aldehydes, and excellent conversions and chemoselectivities were achieved with sodium formate as reductant in neat water.

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

Similar content being viewed by others

References

  1. A. Chanda, V.V. Fokin, Chem. Rev. 109, 725 (2009)

    Article  CAS  Google Scholar 

  2. C.J. Li, L. Chen, Chem. Soc. Rev. 35, 68 (2006)

    Article  Google Scholar 

  3. F. Joo, Acc. Chem. Res. 35, 738 (2002)

    Article  CAS  Google Scholar 

  4. X.F. Wu, J.L. Xiao, Chem. Commun. 2449 (2007)

  5. X.F. Wu, C. Wang, J.L. Xiao, Platinum Metals Rev. 54, 3 (2010)

    Article  CAS  Google Scholar 

  6. J. Canivet, G. Labat, H. Stoeckli-Evans, G. Suss-Fink, Eur. J. Inorg. Chem. 4493 (2005)

  7. P. Stepnicka, J. Ludvik, J. Canivet, G. Suss-Fink, Inorg. Chim. Acta 359, 2369 (2006)

    Article  CAS  Google Scholar 

  8. J. Canivet, G. Suss-Fink, Green Chem. 9, 391 (2007)

    Article  CAS  Google Scholar 

  9. J. Canivet, G. Suss-Fink, P. Stepnicka, Eur. J. Inorg. Chem. 4736 (2007)

  10. K.H. Shaughnessy, Chem. Rev. 109, 643 (2009)

    Article  CAS  Google Scholar 

  11. F. Joo, A. Benyei, J. Organomet. Chem. 363, C19 (1989)

    Article  CAS  Google Scholar 

  12. A. Benyei, F. Joo, J. Mol. Catal. 58, 151 (1990)

    Article  CAS  Google Scholar 

  13. R. Bar, Y. Sasson, J. Blum, J. Mol. Catal. 26, 327 (1984)

    Article  CAS  Google Scholar 

  14. R. Bar, L.K. Bar, Y. Sasson, J. Blum, J. Mol. Catal. 33, 161 (1985)

    Article  CAS  Google Scholar 

  15. S. Ogo, N. Makihara, Y. Watanabe, Organometallics 18, 5470 (1999)

    Article  CAS  Google Scholar 

  16. N. Makihara, S. Ogo, Y. Watanabe, Organometallics 20, 497 (2001)

    Article  CAS  Google Scholar 

  17. S. Ogo, N. Makihara, Y. Kaneko, Y. Watanabe, Organometallics 20, 4903 (2001)

    Article  CAS  Google Scholar 

  18. A.N. Ajjou, J. Pinet, J. Mol. Catal. A: Chem. 214, 203 (2004)

    Article  CAS  Google Scholar 

  19. S. Bolano, L. Gonsalvi, F. Zanobini, F. Vizza, V. Bertolasi, A. Romerosa, M. Peruzzini, J. Mol. Catal. A: Chem. 224, 61 (2004)

    Article  CAS  Google Scholar 

  20. X. Wu, J. Liu, X. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. Ruan, J. Xiao, Angew. Chem. Int. Ed. 45, 6718 (2006)

    Article  CAS  Google Scholar 

  21. C.A. Mebi, R.P. Nair, B.J. Frost, Organometallics 26, 429 (2007)

    Article  CAS  Google Scholar 

  22. Z.S. Liu, G.L. Rempel, J. Mol. Catal. A: Chem. 278, 228 (2007)

    Article  CAS  Google Scholar 

  23. Z.S. Liu, G.L. Rempel, J. Appl. Polym. Sci. 108, 3262 (2008)

    Article  CAS  Google Scholar 

  24. Y. Himeda, N. Onozawa-Komatsuzaki, S. Miyazawa, H. Sugihara, T. Hirose, K. Kasuga, Chem. Eur. J. 14, 11076 (2008)

    Article  CAS  Google Scholar 

  25. J. Li, Y. Zhang, D. Han, G. Jia, J. Gao, L. Zhong, C. Li, Green Chem. 10, 608 (2008)

    Article  CAS  Google Scholar 

  26. L. He, J. Ni, L.-C. Wang, F.-J. Yu, Y. Cao, H.-Y. He, K.-N. Fan, Chem. Eur. J. 15, 11833–11836 (2009)

    Article  CAS  Google Scholar 

  27. H. Cheng, R. Liu, J. Hao, Q. Wang, Y. Yu, S. Cai, F. Zhao, Appl. Organometal. Chem. 24, 763–766 (2010)

    Article  CAS  Google Scholar 

  28. C. Leiva, H.C. Lo, R.H. Fish, J. Organomet. Chem. 695, 145 (2010)

    Article  CAS  Google Scholar 

  29. Z. Zhou, L. Wu, Catal. Commun. 9, 2539 (2008)

    Article  CAS  Google Scholar 

  30. T. Kofoed, H.F. Hansen, H. Ørum, T. Koch, J. Peptide Sci. 7, 402 (2001)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support of this work by the Natural Science Foundation of Hubei Province (2007ABA291, 2008CDA067) is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Zhongqiang Zhou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Huo, H., Zhou, Z., Zhang, A. et al. Ruthenium(II)-catalyzed transfer hydrogenation of aldehydes with new water-soluble monotosylated ethylenediamines as ligands. Res Chem Intermed 38, 261–268 (2012). https://doi.org/10.1007/s11164-011-0345-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-011-0345-4

Keywords

Navigation