Skip to main content
SpringerLink
Log in

Regioselective homogeneous hydrogenation of heteroaromatic nitrogen compounds by use of [RuH(CO)(NCMe)2(PPh3)2]BF4 as the precatalyst

  • Full Papers
  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Summary

The complex [RuH(CO)(NCMe)2(PPh3)2]BF4 (1) is an efficient and regioselective catalyst precursor for the hydrogenation of polyaromatic nitrogen compounds such as quinoline (Q), isoquinoline (iQ), indole (ln), 5,6- and 7,8-benzoquinoline (BQ) and acridine (A) under relatively mild reaction conditions (125 °C, 4 atm H2). The order of individual initial rates was: A > Q > 5,6-BQ > 7,8-BQ > ln > iQ, reflecting both steric and electronic effects. For the regioselective homogeneous hydrogenation of A to 9,10-dihydroacridine (DHA) catalysed by complex (1), a kinetic study was carried out; the experimentally determined rate law was r = k 1 [Ru] [H2]. These findings are consistent with a mechanism involving the hydrogenation of [RuH(CO)(A)(NCMe)(PPh3)2]BF4 to yield DHA and the unsaturated species [RuH(CO)(NCMe)(PPh3)2]BF4 in the rate-determining step.

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

Similar content being viewed by others

References

  1. R. H. Fish, J. N. Michaels, R. S. Moore and H. Heinemann, J. Catal., 123, 74 (1990).

    Google Scholar 

  2. R. H. Fish, J. L. Tan and A. D. Thormodsen, J. Org. Chem., 49, 4500 (1984).

    Google Scholar 

  3. R. H. Fish, H. S. Kim, J. E. Babin and R. D. Adams, Organometallics, 7, 2250 (1988).

    Google Scholar 

  4. E. Baralt, S. J. Smith, J. Hurwitz, I. T. Horváth and R. H. Fish, J. Am. Chem. Soc., 114, 5187 (1992).

    Google Scholar 

  5. R. A. Sánchez-Delgado and E. González, Polyhedron, 8, 1431 (1989).

    Google Scholar 

  6. R. A. Sánchez-Delgado, D. Rondón, A. Andriollo, V. Herrera, G. Martín and B. Chaudret, Organometallics, 12, 4291 (1993).

    Google Scholar 

  7. M. Rosales, Y. Alvarado, M. Boves, R. Rubio, R. Sánchez- Delgado and H. Soscún, Transition Met. Chem., 20, 246 (1995).

    Google Scholar 

  8. R. A. Sánchez-Delgado, M. Rosales and A. Andriollo, Inorg. Chem., 30, 1170 (1991).

    Google Scholar 

  9. M. Rosales, A. González, Y. Alvarado, R. Rubio, A. Andriollo and R. A. Sánchez-Delgado, J. Mol. Catal., 75, 1 (1992).

    Google Scholar 

  10. M. Rosales, Y. Alvarado, N. Gallardo and R. Rubio, Transition Met. Chem., 20, 242 (1995).

    Google Scholar 

  11. J. Casado, M. A. López-Quintela and F. M. Lorenzo-Barral, J. Chem. Ed., 63, 450 (1986).

    Google Scholar 

  12. E. Brunner, J. Chem. Eng. Data, 30, 269 (1985).

    Google Scholar 

  13. C. L. Young (Ed.), Solubility Data Series, Pergamon, Oxford, 1981, Vol. 5/6, pp. 176, 420.

    Google Scholar 

  14. R. H. Crabtree and D. R. Anton, Organometallics, 2, 855 (1983).

    Google Scholar 

  15. C. De La Cruz and N. Sheppard, J. Mol. Struct., 224, 141 (1990).

    Google Scholar 

  16. C. De La Cruz and D. A. Morales, Act. Cient. Venez., 43, 269 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Inorganic Chemistry Laboratory, Facultad de Ciencias, La Universidad del Zulia (LUZ), Apdo. 526, Maracaibo, Venezuela

    Merlin Rosales, Janeth Navarro, Ligbel Sánchez, Angel González, Ysaías Alvarado, Raúl Rubio, Carlos De La Cruz & Tamara Rajmankina

  2. Molecular and Atomic Spectroscopy Laboratory, Facultad de Ciencias, La Universidad del Zulia (LUZ), Apdo. 526, Maracaibo, Venezuela

    Carlos De La Cruz & Tamara Rajmankina

Authors
  1. Merlin Rosales
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Janeth Navarro
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ligbel Sánchez
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Angel González
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ysaías Alvarado
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Raúl Rubio
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Carlos De La Cruz
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Tamara Rajmankina
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rosales, M., Navarro, J., Sánchez, L. et al. Regioselective homogeneous hydrogenation of heteroaromatic nitrogen compounds by use of [RuH(CO)(NCMe)2(PPh3)2]BF4 as the precatalyst. Transition Met Chem 21, 11–15 (1996). https://doi.org/10.1007/BF00166004

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00166004

Keywords

Search

Navigation