SpringerLink
Log in

Carbon—carbon and carbon—nitrogen bond formation reactions catalyzed by the magnesium and calcium acenaphthene-1,2-diimine complexes

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

Abstract

A mixture of allylbromide and diphenylacetonitrile is reduced to afford 2,2-diphenylpentene-4-nitrile as a major product in the presence of catalytic amounts of the magnesium complex (dpp-bian)Mg(thf)3 (dpp-bian is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene dianion). The overall conversion of nitrile is 71% within 3 h at 85 °С. 4,4-Diphenylbutene-1 and diphenylmethane are by-products in this process. Complexes (dpp-bian)Mg(thf)3 and (dpp-bian)Ca(thf)4 (in an amount of 0.5—5 mol.%) catalyze the intramolecular hydroamination of some aminopentenes and aminohexenes with the conversion from 67 to 99%.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Germany)

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. I. Ullah, M. Nawaz, A. Villinger, P. Langer, Tetrahedron Lett., 2011, 52, 1888.

    Article  CAS  Google Scholar 

  2. R. van Asselt, C. J. Elsevier, Tetrahedron, 1994, 50, 323.

    Article  CAS  Google Scholar 

  3. R. van Asselt, C. J. Elsevier, Organometallics, 1994, 13, 1972.

    Article  CAS  Google Scholar 

  4. E. Fillion, V. E. Tré panier, J. J. Heikkinen, A. A. Remorova, R. J. Carson, J. M. Goll, A. Seed, Organometallics, 2009, 28, 3518.

    Article  CAS  Google Scholar 

  5. A. M. Kluwer, T. S. Koblenz, T. Jonischkeit, K. Woelk, C. J. Elsevier, J. Am. Chem. Soc., 2005, 127, 15470.

    Article  CAS  PubMed  Google Scholar 

  6. H. Guo, Z. Zheng, F. Yu, S. Ma, A. Holuigue, D. S. Tromp, C. J. Elsevier, Y. Yu, Angew. Chem., Int. Ed., 2006, 45, 4997.

    Article  CAS  Google Scholar 

  7. M. J. Supej, A. Volkov, L. Darko, R. A. West, J. M. Darmon, C. E. Schulz, K. A. Wheeler, H. M. Hoyt, Polyhedron, 2016, 114, 403.

    Article  CAS  Google Scholar 

  8. F. S. Wekesa, R. Arias-Ugarte, L. Kong, Z. Sumner, G. P. McGovern, M. Findlater, Organometallics, 2015, 34, 5051.

    Article  CAS  Google Scholar 

  9. M. N. Alnajrani, S. A. Alshmimri, O. A. Alsager, RSC Adv., 2016, 6, 113803.

    Article  CAS  Google Scholar 

  10. G. **, D. Zhang, J. Polym. Sci., Part A: Polym. Chem., 2004, 42, 1018.

    Article  CAS  Google Scholar 

  11. J. A. S. Bomfim, M. L. Dias, C. A. L. Filgueiras, F. Peruch, A. Deffieux, Catal. Today, 2008, 133, 879.

    Article  CAS  Google Scholar 

  12. J.-C. Yuan, L. C. Silva, P. T. Gomes, P. Valerga, J. M. Campos, M. R. Ribeiro, J. C. W. Chien, M. M. Marques, Polymer, 2005, 46, 2122.

    Article  CAS  Google Scholar 

  13. H.-R. Liu, P. T. Gomes, S. I. Costa, M. T. Duarte, R. Branquinho, A. C. Fernandes, J. C. W. Chien, R. P. Singh, M. M. Marques, J. Organomet. Chem., 2005, 690, 1314.

    Article  CAS  Google Scholar 

  14. J. Yuan, F. Wang, B. Yuan, Z. Jia, F. Song, J. Li, J. Mol. Catal. A Chem., 2013, 370, 132.

    Article  CAS  Google Scholar 

  15. J. Yuan, Z. Zhang, W. Xu, J. Zhao, Y. Mu, J. Chen, Transit. Met. Chem., 2014, 39, 769.

    Article  CAS  Google Scholar 

  16. J. M. Rose, A. E. Cherian, G. W. Coates, J. Am. Chem. Soc., 2006, 128, 4186.

    Article  CAS  PubMed  Google Scholar 

  17. C. A. Figueira, A. F. G. Ribeiro, C. S. B. Gomes, A. C. Fernandes, L. H. Doerrer, P. T. Gomes, J. Brazilian Chem. Soc., 2014, 25, 2295.

    CAS  Google Scholar 

  18. L. Zhu, D. Zang, Y. Wang, Y. Guo, B. Jiang, F. He, Z. Fu, Z. Fan, M. A. Hickner, Z.-K. Liu, Organometallics, 2017, 36, 1196.

    Article  CAS  Google Scholar 

  19. R. van Asselt, E. E. C. G. Gielens, R. E. Rulke, K. Vrieze, C. J. Elsevier, J. Am. Chem. Soc., 1994, 116, 977.

    Article  CAS  Google Scholar 

  20. A. Scarel, M. R. Axet, F. Amoroso, F. Ragaini, C. J. Elsevier, A. Holuigue, C. Carfagna, L. Mosca, B. Milani, Organometallics, 2008, 27, 1486.

    Article  CAS  Google Scholar 

  21. F. Amoroso, E. Zangrando, C. Carfagna, C. Müller, D. Vogt, M. Hagar, F. Ragaini, B. Milani, Dalton Trans., 2013, 42, 14583.

    Article  CAS  PubMed  Google Scholar 

  22. V. Rosar, A. Meduri, T. Montini, F. Fini, C. Carfagna, P. Fornasiero, G. Balducci, E. Zangrando, B. Milani, ChemCatChem, 2014, 6, 2403.

    Article  CAS  Google Scholar 

  23. Z. Chen, W. Liu, O. Daugulis, M. Brookhart, J. Am. Chem. Soc., 2016, 138, 16120.

    Article  CAS  PubMed  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  26. I. L. Fedushkin, A. A. Skatova, V. K. Cherkasov, V. A. Chudakova, S. Dechert, M. Hummert, H. Schumann, Chem. — A Eur. J., 2003, 9, 5778.

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  28. 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  PubMed  Google Scholar 

  29. I. L. Fedushkin, A. S. Nikipelov, A. G. Morozov, A. A. Ska tova, A. V. Cherkasov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 255.

    Article  CAS  PubMed  Google Scholar 

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

    Google Scholar 

  31. S. M. Coman, V. I. Parvulescu, Org. Process Res. Dev., 2015, 19, 1327–1355.

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  35. A. L. Reznichenko, K. C. Hultzsch, Org. React., 2015, 88, 1.

    Google Scholar 

  36. S. R. Chemler, Org. Biomol. Chem., 2009, 7, 3009.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. G. Zi, Dalton Trans., 2009, 9101.

    Google Scholar 

  38. K. D. Hesp, M. Stradiotto, ChemCatChem, 2010, 2, 1192.

    Article  CAS  Google Scholar 

  39. A. L. Reznichenko, A. J. Nawara-Hultzsch, K. C. Hultzsch, in Stereoselective Form. Amin., Springer, 2013, 191.

    Book  Google Scholar 

  40. E. Bernoud, C. Lepori, M. Mellah, E. Schulz, J. Hannedouche, Catal. Sci. Technol., 2015, 5, 2017.

    Article  CAS  Google Scholar 

  41. A. K. Gupta, K. L. Hull, Synlett, 2015, 26, 1779.

    Article  CAS  Google Scholar 

  42. V. Rodriguez-Ruiz, R. Carlino, S. Bezzenine-Lafollée, R. Gil, D. Prim, E. Schulz, J. Hannedouche, Dalton Trans., 2015, 44, 12029.

    Article  CAS  PubMed  Google Scholar 

  43. I. L. Fedushkin, A. G. Morozov, O. V. Rassadin, G. K. Fukin, Chem. Eur. J., 2005, 11, 5749.

    Article  CAS  PubMed  Google Scholar 

  44. I. L. Fedushkin, V. M. Makarov, E. C. E. Rosenthal, G. K. Fukin, Eur. J. Inorg. Chem., 2006, 827.

    Google Scholar 

  45. M. Yasuda, T. Saito, M. Ueba, A. Baba, Angew. Chem., Int. Ed., 2004, 43, 1414.

    Article  CAS  Google Scholar 

  46. SDBSWeb; http://sdbs.db.aist.go.jp (NationalInstitute ofAdvanced IndustrialScience and Technology), 2017.

  47. R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc., Trans., 1915, 107, 1080.

    Article  CAS  Google Scholar 

  48. M. Arrowsmith, M. S. Hill, G. Kociok-Kohn, Organometallics, 2014, 33, 206.

    Article  CAS  Google Scholar 

  49. A. Cimino, F. Moscatelli, F. Ferretti, F. Ragaini, S. Germain, J. Hannedouche, E. Schulz, L. Luconi, A. Rossin, G. Giambastiani, New J. Chem., 2016, 40, 10285.

    Article  CAS  Google Scholar 

  50. A. Paulovicova, U. El-Ayaan, K. Shibayama, T. Morita, Y. Fukuda, Eur. J. Inorg. Chem., 2001, 2641.

    Google Scholar 

  51. M. R. Crimmin, M. Arrowsmith, A. G. M. Barrett, I. J. Cas ely, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc., 2009, 131, 9670.

    Article  CAS  PubMed  Google Scholar 

  52. J. Y. Kim, T. Livinghouse, Org. Lett., 2005, 7, 1737.

    Article  CAS  PubMed  Google Scholar 

  53. G. Lai, W. K. Anderson, Tetrahedron Lett., 1993, 34, 6849.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhni Novgorod, Russian Federation

    A. M. Yakub, M. V. Moskalev, N. L. Bazyakina & 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. 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 I. P. Beletskaya

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0473—0478, March, 2018.

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. Carbon—carbon and carbon—nitrogen bond formation reactions catalyzed by the magnesium and calcium acenaphthene-1,2-diimine complexes. Russ Chem Bull 67, 473–478 (2018). https://doi.org/10.1007/s11172-018-2095-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-018-2095-6

Key words

Search

Navigation