Skip to main content
SpringerLink
Log in

Novel olefin metathetis catalysts with fluorinated N-alkyl-N´-arylimidazolin-2-ylidene ligands

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Novel ruthenium carbene complexes bearing unsymmetrical NHC-ligands based on N-alkyl-N´-arylimidazoline with hexafluoroisopropylmethoxy group in para-position of N-aryl moiety have been synthesized. Catalytic activity of complexes obtained was investigated on model reactions of intra- and intermolecular olefin metathesis.

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. I. C. Stewart, T. Ung, A. A. Pletnev, J. M. Berlin, R. H. Grubbs, Y. Schrodi, Org. Lett., 2007, 9, 1589.

    Article  CAS  Google Scholar 

  2. C. Samojołowicz, M. Bieniek, K. Grela, Chem. Rev., 2009, 109, 3708.

    Article  Google Scholar 

  3. G. C. Vougioukalakis, R. H. Grubbs, Chem. Rev., 2010, 110, 1746.

    Article  CAS  Google Scholar 

  4. M. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature, 2014, 510, 485.

    Article  CAS  Google Scholar 

  5. S. J. Connon, S. Blechert, Recent Advances in Alkene Metathesis, in Ruthenium Catalysts and Fine Chemistry, Eds C. Bruneau, P. H. Dixneuf, Springer, Heidelberg, 2004, 93.

    Chapter  Google Scholar 

  6. A. H. Hoveyda, A. R. Zhugralin, Nature, 2007, 450, 243.

    Article  CAS  Google Scholar 

  7. P. H. Deshmukh, S. Blechert, Dalton Trans., 2007, 2479.

    Google Scholar 

  8. K. Grela, Olefin Metathesis Theory and Practice, J. Wiley & Sons: Hoboken, New Jersey, 2014.

    Book  Google Scholar 

  9. J. Tornatzky, A. Kannenberg, S. Blechert, Dalton Trans., 2012, 41, 8215.

    Article  CAS  Google Scholar 

  10. P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.

    Book  Google Scholar 

  11. K. L. Kirk, J. Fluorine Chem., 2006, 127, 1013.

    Article  CAS  Google Scholar 

  12. D. O´Hagan, Chem. Soc. Rev., 2008, 37, 308.

    Article  Google Scholar 

  13. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev., 2011, 111, 455.

    Article  CAS  Google Scholar 

  14. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, UK, 2006.

    Book  Google Scholar 

  15. M. Jagodzinska, F. Huguenot, G. Candiani, M. Zanda, ChemMedChem, 2009, 4, 49.

    Article  CAS  Google Scholar 

  16. R. C. da Costa, J. A. Gladysz, Chem. Commun., 2006, 2619.

    Google Scholar 

  17. R. C. da Costa, J. A. Gladysz, Adv. Synth. Catal., 2007, 349, 243.

    Article  Google Scholar 

  18. R. Tuba, R. C. da Costa, H. S. Bazzi, J. A. Gladysz, ACS Catal., 2012, 2, 155.

    Article  CAS  Google Scholar 

  19. M. Matsugi, D. P. Curran, J. Org. Chem., 2005, 70, 1636.

    Article  CAS  Google Scholar 

  20. S. Leach, C. J. Cordier, D. Morton, G. J. McKierman, S. Warriner, A. Nelson, J. Org. Chem., 2008, 73, 2753.

    Article  CAS  Google Scholar 

  21. M. Matsugi, Y. Kobayashi, N. Suzumura, Y. Tsuchiya, T. Shioiri, J. Org. Chem., 2010, 75, 7905.

    Article  CAS  Google Scholar 

  22. J. Kvíčala, M. Schindler, V. Kelbichová, M. Babunìk, M. Rybáčková, M. Kvíčlová, J. Cvačka, A. Březinová, J. Fluorine Chem., 2013, 153, 12.

    Article  Google Scholar 

  23. M. Babune´k, O. Šimůnek, J. Hošek, M. Rybáčková, J. Cvačka, A. Březinová, J. Kvíčala, J. Fluorine Chem., 2014, 161, 66.

    Article  Google Scholar 

  24. Q. Yao, Y. Zhang, J. Am. Chem. Soc., 2004, 126, 74.

    Article  CAS  Google Scholar 

  25. Y. Kobayashi, S. Inukai, N. Kondo, T. Watanabe, Y. Sugiyama, H. Hamamoto, T. Shioiri, M. Matsugi, Tetrahedron Lett., 2015, 56, 1363.

    Article  CAS  Google Scholar 

  26. T. S. Halbach, S. Mix, D. Fischer, S. Maechling, J. O. Krause, C. Sievers, S. Blechert, O. Nuyken, M. R. Buchmeiser, J. Org. Chem., 2005, 70, 4687.

    Article  CAS  Google Scholar 

  27. S. Monfette, K. D. Camm, S. I. Gorelsky, D. E. Fogg, Organometallics, 2009, 28, 944.

    Article  CAS  Google Scholar 

  28. S. Fustero, A. Simon-Fuentes, P. Barrio, G. Haufe, Chem. Rev., 2015, 115, 871.

    Article  CAS  Google Scholar 

  29. V. Siano, I. d´Auria, F. Grisi, C. Costabile, P. Longo, Cent. Eur. J. Chem., 2011, 9, 605.

    CAS  Google Scholar 

  30. A. Furstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer, O. R. Thiel, Chem. Eur. J., 2001, 7, 3236.

    Article  CAS  Google Scholar 

  31. T. Ritter, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc., 2006, 128, 11768.

    Article  CAS  Google Scholar 

  32. D. R. Anderson, D. J. O´Leary, R. H. Grubbs, Chem. Eur. J., 2008, 14, 7536.

    Article  CAS  Google Scholar 

  33. S. M. Masoud, A. K. Mailyan, V. Dorcet, T. Roisnel, P. H. Dixneuf, C. Bruneau, S. N. Osipov, Organometallics, 2015, 34, 2305.

    Article  CAS  Google Scholar 

  34. S. M. Masoud, A. K. Mailyan, A. S. Peregudov, C. Bruneau, S. N. Osipov, Mendeleev Commun., 2016, 26, 474.

    Article  CAS  Google Scholar 

  35. S. M. Masoud, M. A. Topchiy, A. S. Peregudov, T. Roisnel, P. H. Dixneuf, C. Bruneau, S. N. Osipov, J. Fluorine Chem., 2017, 200, 66.

    Article  CAS  Google Scholar 

  36. J. S. Kingsbury, J. P. A. Harrity, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc., 1999, 121, 791.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    S. M. Masoud, T. R. Akmalov, O. I. Artyushin & S. N. Osipov

  2. CNRS -Universitŭ de Rennes 1, Institute des Sciences Chimique de Rennes, Organomŭtalliques: Matŭriaux et Catalyse, Centre for Catalysis and Green Chemistry, Campus de Beaulieau, 35042, Rennes, France

    C. Bruneau

Authors
  1. S. M. Masoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. R. Akmalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. I. Artyushin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. Bruneau
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. N. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. N. Osipov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences G. A. Abakumov on the occasion of his 80th birthday.

UMR 6226 CNRS-Universiteì de Rennes 1, Institut des Sciences Chimiques de Rennes, Organomйtalliques: Matériaux et Catalyse, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes, France.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1601—1606, September, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Masoud, S.M., Akmalov, T.R., Artyushin, O.I. et al. Novel olefin metathetis catalysts with fluorinated N-alkyl-N´-arylimidazolin-2-ylidene ligands. Russ Chem Bull 66, 1601–1606 (2017). https://doi.org/10.1007/s11172-017-1930-5

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1930-5

Key words

Search

Navigation