Skip to main content
SpringerLink
Log in

Hydroamination of 2-vinylpyridine, styrene, and isoprene with pyrrolidine catalyzed by alkali and alkaline-earth metal complexes

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

Abstract

The complexes (dpp-bian)Mg(thf)3, (dpp-bian)Ca(thf)4 and (dpp-bian)Mg(pyr)3 (dpp-bian is the 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene dianion; pyr is the pyrrolidine) catalyze the addition of pyrrolidine to 2-vinylpyridine at room temperature. The compound (dppbian)Mg[N(SiMe3)2] containing a dpp-bian radical anion catalyzes the addition of pyrrolidine to styrene at 60 °C. The dpp-bian radical anion lithium-sodium salt [(dpp-bian)Li{N-(SiMe3)2}][Na(C7H8)] is an active catalyst of the addition of pyrrolidine to styrene and isoprene at 60 °C. In all the case, the content of the catalyst was from 1 to 2 mol.%. For styrene and 2-vinylpyridine, the reactions proceeded with the formation of anti-Markovnikov addition product, while 1,4-addition product was obtained in the case of isoprene.

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. L. Huang, M. Arndt, K. Gooßen, H. Heydt, L. J. Gooßen, Chem. Rev., 2015, 115, 2596.

  2. N. T. Patil, R. D. Kavthe, V. S. Shinde, Tetrahedron, 2012, 68, 8079.

    Article  CAS  Google Scholar 

  3. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev., 2011, 111, 1657.

    Article  CAS  Google Scholar 

  4. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev., 2008, 108, 3795.

    Article  Google Scholar 

  5. J. Hannedouche, E. Schulz, Chem. Eur. J., 2013, 19, 4972.

    Article  CAS  Google Scholar 

  6. P. Yin, T. P. Loh, Org. Lett., 2009, 11, 3791.

    Article  CAS  Google Scholar 

  7. I. V. Basalov, S. C. Roca, D. M. Lyubov, A. N. Selikhov, G. K. Fukin, Y. Sarazin, J.-F. Carpentier, A. A. Trifonov, Inorg. Chem., 2014, 53, 1654.

    Article  CAS  Google Scholar 

  8. S. Germain, E. Schulz, J. Hannedouche, ChemCatChem, 2014, 6, 2065.

    Article  CAS  Google Scholar 

  9. A. A. Kissel, T. V. Mahrova, D. M. Lyubov, A. V. Cherkasov, G. K. Fukin, A. A. Trifonov, I. del Rosal, L. Maron, Dalton Trans., 2015, 44, 12137.

    Article  CAS  Google Scholar 

  10. J.-S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc., 2003, 125, 12584.

    Article  CAS  Google Scholar 

  11. D. V. Gribkov, K. C. Hultzsch, F. Hampel, J. Am. Chem. Soc., 2006, 128, 3748.

    Article  CAS  Google Scholar 

  12. A. L. Reznichenko, H. N. Nguyen, K. C. Hultzsch, Angew. Chem., Int. Ed., 2010, 49, 8984.

    Article  CAS  Google Scholar 

  13. A. L. Reznichenko, K. C. Hultzsch, Organometallics, 2013, 32, 1394.

    Article  CAS  Google Scholar 

  14. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Chem. Eur. J., 2013, 19, 13445.

    Article  CAS  Google Scholar 

  15. G. M. Barrett, C. Brinkmann, M. R. Crimmin, M. S. Hill, P. Hunt, P. A. Procopiou, J. Am. Chem. Soc., 2009, 131, 12906.

    Article  CAS  Google Scholar 

  16. C. Brinkmann, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc., 2012, 134, 2193.

    Article  CAS  Google Scholar 

  17. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Angew. Chem., Int. Ed., 2012, 51, 4943.

    Article  CAS  Google Scholar 

  18. X. Zhang, T. J. Emge, K. C. Hultzsch, Angew. Chem., Int. Ed., 2012, 51, 394.

    Article  CAS  Google Scholar 

  19. M. S. Hill, D. J. Liptrot, C. Weetman, Chem. Soc. Rev., 2016, 45, 972.

    Article  CAS  Google Scholar 

  20. Y. Sarazin, J.-F. Carpentier, Chem. Rec., 2016, doi:10.1002/tcr.201600067.

    Google Scholar 

  21. P. Horrillo-Martínez, K. C. Hultzsch, A. Gil, V. Branchadell, Eur. J. Org. Chem., 2007, 3311.

    Google Scholar 

  22. M. Beller, C. Breindl, Tetrahedron, 1998, 54, 6359.

    Article  CAS  Google Scholar 

  23. I. L. Fedushkin, A. S. Nikipelov, A. G. Morozov, A. A. Skatova, A. V. Cherkasov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 255.

    Article  CAS  Google Scholar 

  24. I. L. Fedushkin, O. V. Kazarina, A. N. Lukoyanov, A. A. Skatova, N. L. Bazyakina, A. V. Cherkasov, E. Palamidis, Organometallics, 2015, 34, 1498.

    Article  CAS  Google Scholar 

  25. O. V. Kazarina, M. V. Moskalev, I. L. Fedushkin, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 32 [Izv. Akad. Nauk, Ser. Khim., 2015, 32].

    Article  CAS  Google Scholar 

  26. I. L. Fedushkin, M. V. Moskalev, E. V. Baranov, G. A. Abakumov, J. Organomet. Chem., 2013, 747, 235.

    Article  CAS  Google Scholar 

  27. M. V. Moskalev, A. M. Yakub, A. G. Morozov, E. V. Baranov, O. V. Kazarina, I. L. Fedushkin, Eur. J. Org. Chem., 2015, 5781.

    Google Scholar 

  28. I. L. Fedushkin, A. S. Nikipelov, K. A. Lyssenko, J. Am. Chem. Soc., 2010, 132, 7874.

    Article  CAS  Google Scholar 

  29. I. L. Fedushkin, M. V. Moskalev, A. N. Lukoyanov, A. N. Tishkina, E. V. Baranov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 11264.

    Article  CAS  Google Scholar 

  30. I. L. Fedushkin, N. M. Khvoinova, A. A. Skatova, G. K. Fukin, Angew. Chem., Int. Ed., 2003, 42, 5223.

    Article  CAS  Google Scholar 

  31. I. L. Fedushkin, Proc. International Conference on Organometallic and Coordination Chemistry (N. Novgorod, September 2–8, 2008), N. Novgorod,2010, S7.

    Google Scholar 

  32. I. L. Fedushkin, A. A. Skatova, V. A. Chudakova, G. K. Fukin, S. Dechert, H. Schumann, Eur. J. Inorg. Chem., 2003, 3336.

    Google Scholar 

  33. I. L. Fedushkin, A. G. Morozov, V. A. Chudakova, G. K. Fukin, V. K. Cherkasov, Eur. J. Inorg. Chem., 2009, 4995.

    Google Scholar 

  34. I. L. Fedushkin, V. A. Chudakova, G. K. Fukin, S. Dechert, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 2744 [Izv. Akad. Nauk, Ser. Khim., 2004, 2641].

    Article  CAS  Google Scholar 

  35. H. Schumann, M. Hummert, A. N. Lukoyanov, I. L. Fedushkin, Chem. Eur. J. 2007, 13, 4216.

    Article  CAS  Google Scholar 

  36. I. L. Fedushkin, A. N. Lukoyanov, M. Hummert, H. Schumann, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 1765 [Izv. Akad. Nauk, Ser. Khim., 2007, 1702].

    Article  CAS  Google Scholar 

  37. M. Beller, H. Trauthwein, M. Eichberger, C. Breindl, T. E. Müller, Eur. J. Inorg. Chem., 1999, 1121.

    Google Scholar 

  38. Bruker (2012). APEX2. BrukerAXS Inc., Madison, Wisconsin, USA.

  39. Bruker (2001). SADABS. BrukerAXS Inc., Madison, Wisconsin, USA.

  40. Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.

  41. G. M. Sheldrick, ActaCryst., 2015, A71, 3.

    Google Scholar 

  42. G. M. Sheldrick, ActaCryst., 2015, C71, 3.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603137, Nizhny Novgorod, Russian Federation

    A. M. Yakub, M. V. Moskalev, N. L. Bazyakina, A. V. Cherkasov, A. S. Shavyrin & I. L. Fedushkin

Authors
  1. A. M. Yakub
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Moskalev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. L. Bazyakina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Cherkasov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. S. Shavyrin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. L. Fedushkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. L. Fedushkin.

Additional information

Dedicated to Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2887–2894, December, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yakub, A.M., Moskalev, M.V., Bazyakina, N.L. et al. Hydroamination of 2-vinylpyridine, styrene, and isoprene with pyrrolidine catalyzed by alkali and alkaline-earth metal complexes. Russ Chem Bull 65, 2887–2894 (2016). https://doi.org/10.1007/s11172-016-1673-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1673-8

Key words

Search

Navigation