Skip to main content
SpringerLink
Log in

Negishi reaction in the synthesis of (ω-hydroxyalkyl-1-en-1-yl selenides

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

Abstract

A regio- and stereoselective method for preparation of aryl ω-hydroxyalk-1-en-1-ylselenides was developed. It is based on the Negishi reaction of Zr-catalyzed methylalumination of ω-hydroxyalkynes with following selenation with diaryl diselenide.

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

References

  1. M. V. Lesnichaya, A. N. Sapozhnikov, B. G. Sukhov, Russ. Chem. Bull., 2020, 69, 1979; DOI: https://doi.org/10.1007/s11172-020-2988-z.

    Article  CAS  Google Scholar 

  2. S. E. Yagunov, S. V. Kholshin, N. V. Kandalintseva, O. I. Prosenko, Russ. Chem. Bull., 2021, 70, 195; DOI: https://doi.org/10.1007/s11172-021-3077-7.

    Article  CAS  Google Scholar 

  3. Ya. P. Kuznetsov, D. A. Pitushkin, E. A. Eshtukova-Shcheglova, V. V. Burmistrov, G. M. Butov, I. A. Novakov. Russ. Chem. Bull., 2022, 71, 2467; DOI: https://doi.org/10.1007/s11172-022-3675-z.

    Article  CAS  Google Scholar 

  4. A. V. Finko, A. I. Sokolov, L. A. Vasilyeva, D. A. Skvortsov, A. S. H. Al-Khazraji, E. N. Ofitserov, N. V. Zyk, A. G. Majouga, E. K. Beloglazkina, Russ. Chem. Bull., 2021, 70, 457; DOI: https://doi.org/10.1007/s11172-021-3108-4.

    Article  CAS  Google Scholar 

  5. A. Kunwar, B. Mishra, A. Barik, L. B. Kumbhare, R. Pandey, V. K. Jain, K. I. Priyadarsini, Chem. Res. Toxicol., 2007, 20, 1482; DOI: https://doi.org/10.1021/tx700137a.

    Article  CAS  PubMed  Google Scholar 

  6. H. Takahashi, A. Nishina, R.-h. Fukumoto, H. Kimura, M. Koketsu, H. Ishihara, Eur. J. Pharm. Sci., 2005, 24, 291; DOI: https://doi.org/10.1016/j.ejps.2004.11.004.

    Article  CAS  PubMed  Google Scholar 

  7. Lars-Oliver, K. HelmutSies, Toxicol. Lett., 2003, 140, 125; DOI: https://doi.org/10.1016/S0378-4274(02)00511-8.

    Google Scholar 

  8. K. Laude, C. Thuillez, V. Richard, Am. J. Physiol. Heart Circ. Physiol., 2002, 283, 1418; DOI: https://doi.org/10.1152/ajpheart.00375.2002.

    Article  Google Scholar 

  9. H. Sies, G. E. Arteela, Free Radic. Biol. Med., 2000, 28, 1451; DOI: https://doi.org/10.1016/S0891-5849(00)00253-7.

    Article  CAS  PubMed  Google Scholar 

  10. G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, R. J. Butcher, J. Am. Chem. Soc., 2001, 123, 839; DOI: https://doi.org/10.1021/ja994467p.

    Article  CAS  PubMed  Google Scholar 

  11. G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, R. J. Butcher, Chem. Commun., 1998, 222, 2227; DOI: https://doi.org/10.1039/A805941A.

    Article  Google Scholar 

  12. B. Mishra, K. I. Priyadarsini, H. Mohan, G. Mugesh, Bioorg. Med. Chem. Lett., 2006, 16, 5334; DOI: https://doi.org/10.1016/j.bmcl.2006.07.085.

    Article  CAS  PubMed  Google Scholar 

  13. G. Mugesh, W.-W. du Mont, H. Sies, Chem. Rev., 2001, 101, 2125; DOI: https://doi.org/10.1021/cr000426w.

    Article  CAS  PubMed  Google Scholar 

  14. B. K. Sarma, G. Mugesh, J. Am. Chem. Soc., 2005, 127, 11477; DOI: https://doi.org/10.1021/ja052794t.

    Article  CAS  PubMed  Google Scholar 

  15. A. M. Mickalad, J. M. Faez, L. Chistiaens, S. Kohnen, C. Deby, M. Hoebeke, M. Lamy, G. D. Dupont, Redox Rep., 2004, 9, 81; DOI: https://doi.org/10.1179/135100004225004788.

    Article  Google Scholar 

  16. B. Mishra, A. Barik, A. Kunwar, L. B. Kumbhare, K. I. Priyadarsini, V. K. Jain, Phosphor. Sulfur Silicon, 2008, 183, 1018; DOI: https://doi.org/10.1080/10426500801901046.

    Article  CAS  Google Scholar 

  17. G. Perin, E. J. Lenardão, R. G. Jacob, R. B. Panatieri, Chem. Rev., 2009, 109, 1277; DOI: https://doi.org/10.1021/cr8004394.

    Article  CAS  PubMed  Google Scholar 

  18. I. P. Beletskaya, V. P. Ananikov, Chem. Rev., 2011, 111, 1596; DOI: https://doi.org/10.1021/cr100347k.

    Article  CAS  PubMed  Google Scholar 

  19. I. P. Beletskaya, V. P. Ananikov, Eur. J. Org. Chem., 2007, 3431; DOI: https://doi.org/10.1002/ejoc.200700119.

  20. J. V. Comasseto, J. T. B. Ferreira, N. Petragnani, J. Organomet. Chem., 1981, 216; DOI: https://doi.org/10.1016/S0022-328X(00)85812-X.

  21. J. Gosselck, Angew. Chem., Int. Ed., 1963, 2, 660; DOI: https://doi.org/10.1002/anie.196306601.

    Article  Google Scholar 

  22. K. B. Sharpless, R. F. Lauer, J. Am. Chem. Soc., 1973, 95, 2697; DOI: https://doi.org/10.1021/ja00789a055.

    Article  CAS  Google Scholar 

  23. M. Miyashita, T. Suzuki, M. Hoshino, A. Yoshikoshi, Tetrahedron, 1997, 53, 12469; DOI: https://doi.org/10.1016/S0040-4020(97)00781-3.

    Article  CAS  Google Scholar 

  24. O. S. R. Barros, E. S. Lang, C. A. F. de Oliveira, C. Peppe, G. Zeni, Tetrahedron Lett., 2002, 43, 7921; DOI: https://doi.org/10.1016/S0040-4039(02)01904-4.

    Article  CAS  Google Scholar 

  25. C. Peppe, E. S. Lang, G. N. Ledesma, L. B. Castro, O. S. R. Barros, P. A. Mello, Synlett, 2005, 309, 3091; DOI: https://doi.org/10.1055/s-2005-921931.

    Article  Google Scholar 

  26. G. Zeni, M. P. Stracke, C. W. Nogueira, A. L. Braga, P. H. Menezes, H. A. Stefani, Org. Lett., 2004, 6, 1135; DOI: https://doi.org/10.1021/ol0498904.

    Article  CAS  PubMed  Google Scholar 

  27. X. Huang, L.-S. Zhu, Synth. Commun., 1996, 26, 671; DOI: https://doi.org/10.1080/00397919608086739.

    Article  CAS  Google Scholar 

  28. X. Huang, L.-S. Zhu, J. Chem. Soc., Perkin Trans 1, 1996, 767; DOI: https://doi.org/10.1039/P19960000767.

  29. H. Zhao, M. Cai, Synthesis (Stuttg), 2002, 1347; DOI: https://doi.org/10.1055/s-2002-33123.

  30. V. A. D’yakonov, R. A. Tuktarova, T. V. Tyumkina, L. M. Khalilov, U. M. Dzhemilev, Russ. Chem. Bull., 2010, 59, 1902; DOI: https://doi.org/10.1007/s11172-010-0331-9.

    Article  Google Scholar 

  31. V. A. D’yakonov, L. F. Galimova, T. V. Tyumkina, U. M. Dzhemilev, Russ. J. Org. Chem., 2012, 48, 1; DOI: https://doi.org/10.1134/S1070428012010010.

    Article  Google Scholar 

  32. R. N. Kadikova, I. R. Ramazanov, A. V. Vyatkin, U. M. Dzhemilev, Synthesis, 2017, 49, 4523; DOI: https://doi.org/10.1055/s-0036-1589062.

    Article  CAS  Google Scholar 

  33. D. E. Van Horn, E. Negishi, J. Am. Chem. Soc., 1978, 100, 2252; DOI: https://doi.org/10.1021/ja00475a058.

    Article  CAS  Google Scholar 

  34. J. M. Chong, M. A. Heuft, P. Rabbat, J. Org. Chem., 2000, 65, 5837; DOI: https://doi.org/10.1021/jo000291u.

    Article  CAS  PubMed  Google Scholar 

  35. L. F. Tietze, Th. Eicher, Reaktionen und Synthesen im Organisch-Chemischen Praktikum und Forschungslaboratorium, 2. Aufl., Georg Thieme Verlag, Stuttgart-New York, 1991, 672 pp.

    Book  Google Scholar 

  36. I. Mohammad, J. Mun, A. Onorato, M. D. Morton, A. I. Saleh, M. B. Smith, Tetrahedron Lett., 2017, 58, 4162; DOI: https://doi.org/10.1016/j.tetlet.2017.09.026.

    Article  CAS  Google Scholar 

  37. M. A. Rizvi, S. Guru, T. Naqvi, M. Kumar, N. Kumbhar, S. Akhoon, S. Banday, S. K. Singh, S. Bhushan, G. M. Peerzada, B. A. Shah, Med. Chem. Lett., 2014, 24, 3440; DOI: https://doi.org/10.1016/j.bmcl.2014.05.075.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    R. N. Kadikova, A. V. Vyatkin, A. M. Gabdullin, O. S. Mozgovoj & I. R. Ramazanov

  2. N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    U. M. Dzhemilev

Authors
  1. R. N. Kadikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Vyatkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. M. Gabdullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. S. Mozgovoj
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. U. M. Dzhemilev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. R. Ramazanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. N. Kadikova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was performed under financial support of the Russian Science Foundation (Project No. 19-73-20128). Synthesis of organic diselenides was carried out in the framework of a state task (project No. FMRS-2022-0076) of the Ministry of Science and Higher Education of the Russian Federation. Structural studies were performed in the Center of Collective Usage of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences (CCP of IOC RAS) and the Regional Center of Collective Usage “Agidel” of the Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 1023–1028, April, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kadikova, R.N., Vyatkin, A.V., Gabdullin, A.M. et al. Negishi reaction in the synthesis of (ω-hydroxyalkyl-1-en-1-yl selenides. Russ Chem Bull 72, 1023–1028 (2023). https://doi.org/10.1007/s11172-023-3867-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3867-4

Key words

Search

Navigation