Skip to main content
Log in

Phosphinine – synthesis of a heavy sibling of pyridine (microreview)

  • HETEROCYCLES IN FOCUS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The microreview covers three, most powerful, strategies of the synthesis of phosphinine (systematically called phosphabenzene) starting from pyrylium salts, five-membered heterocycles, and reagents with C≡P bond.

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.

Similar content being viewed by others

References

  1. Ashe, J. A. J. Am. Chem. Soc. 1971, 93, 3293.

    Article  CAS  Google Scholar 

  2. Märkl, G. Angew. Chem. 1966, 78, 907.

    Article  Google Scholar 

  3. Savateev, A.; Vlasenko, Y.; Shtil, N.; Kostyuk, A. Eur. J. Inorg. Chem. 2016, 628.

  4. Nyulaszi, L. Chem. Rev. 2001, 101, 1229.

    Article  CAS  Google Scholar 

  5. Weemers, J. J. M. Phosphinine-Based Ligands: Unique Phosphorus Heterocycles in Homogeneous Catalytic Reactions; Eindhoven: Technische Universiteit Eindhoven, 2014, DOI: https://doi.org/10.6100/IR762991.

    Google Scholar 

  6. Kostenko, N.; Ericsson, C.; Engqvist, E.; Gonzalez, S. V.; Bayer, A. Eur. J. Org. Chem. 2013, 4756.

  7. Mastalir, M.; Kirchner, K. Monatsh. Chem. 2017, 148, 105.

    Article  CAS  Google Scholar 

  8. Muller, C.; Broeckx, L. E. E.; de Krom, I.; Weemers, J. J. M. Eur. J. Inorg. Chem. 2013, 187.

  9. (a) Müller, C.; Broeckx, L. E. E.; de Krom, I.; Weemers, J. J. M. Eur. J. Inorg. Chem. 2013, 187. (b) Corbridge, D. E. C. Phosphorus: Chemistry, Biochemistry, and Technology; Taylor & Francis, 2013, 6th ed.

  10. Märkl, G. Angew. Chem., Int. Ed. 1967, 6, 944.

    Article  Google Scholar 

  11. Van der Velde, N. A.; Korbitz, H. T.; Garner, C. M. Tetrahedron Lett. 2012, 53, 5742.

    Article  Google Scholar 

  12. Muller, C.; Pidko, E. A.; Staring, A. J. P. M.; Lutz, M.; Spek, A. L.; Van Santen, R. A.; Vogt, D. Chem.–Eur. J. 2008, 14, 4899.

    Article  Google Scholar 

  13. Muller, C.; Lopez, L. G.; Kooijman, H.; Spek, A. L.; Vogt, D. Tetrahedron Lett. 2006, 47, 2017.

    Article  Google Scholar 

  14. Muller, C.; Wasserberg, D.; Weemers, J. J. M.; Pidko, E. A.; Hoffmann, S.; Lutz, M.; Spek, A. L.; Meskers, S. C. J.; Janssen, R. A. J.; Van Santen, R. A.; Vogt, D. Chem.–Eur. J. 2007, 13, 4548.

    Article  Google Scholar 

  15. Nagahora, N.; Ogawa, T.; Honda, M.; Fujii, M.; Tokumaru, H.; Sasamori, T.; Shioji K.; Okuma, K. Chem. Lett. 2015, 44, 706.

    Article  CAS  Google Scholar 

  16. Wrackmeyer, B.; Klaus, U. J. Organomet. Chem. 1996, 520, 211.

    Article  CAS  Google Scholar 

  17. Hunter, R. A.; Whitby, R. J.; Light, M. E.; Hursthouse, M. B. Tetrahedron Lett. 2004, 45, 7633.

    Article  CAS  Google Scholar 

  18. Mao, Y.; Mathey F. Chem.–Eur. J. 2011, 17, 10745.

    Article  CAS  Google Scholar 

  19. Wang, H.; Li, C.; Geng, D.; Chen, H.; Duan, Z.; Mathey, F. Chem.–Eur. J. 2010, 16, 10659.

    Article  CAS  Google Scholar 

  20. Grundy, J.; Mathey, F. Angew. Chem., Int. Ed. 2005, 44, 1082.

    Article  CAS  Google Scholar 

  21. (a) Rösch, W.; Regitz, M. Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1986, 41, 931. (b) Habicht, M. H.; Wossidlo, F.; Weber, M.; Muller, C. Chem.–Eur. J. 2016, 22, 12877.

  22. Chen, X.; Alidori, S.; Puschmann, F. F.; Santiso-Quinones, G.; Benko, Z.; Li, Z.; Becker, G.; Grutzmacher, H.-F.; Grutzmacher, H. Angew. Chem., Int. Ed. 2014, 53, 1641.

    Article  CAS  Google Scholar 

  23. (a) Nakajima, K.; Takata, S.; Sakata, K.; Nishibayashi, Y. Angew. Chem., Int. Ed. 2015, 54, 7597. (b) Nakajima, K.; Liang, W.; Nishibayashi, Y. Org. Lett. 2016, 18, 5006.

Download references

Financial support by Polish National Science Centre (UMO-2014/13/N/ST5/01532) is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Paweł Tokarz or Piotr M. Zagórski.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 858–860

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tokarz, P., Zagórski, P.M. Phosphinine – synthesis of a heavy sibling of pyridine (microreview). Chem Heterocycl Comp 53, 858–860 (2017). https://doi.org/10.1007/s10593-017-2138-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2138-1

Keywords

Navigation