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Synthesis of functionalized phosphorus-containing tetraorganosilanes

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Abstract

A convenient synthesis of functionalized β-phosphorus-substituted tetraorganosilanes containing hydrolysis-resistant organosilicon moieties comprises radical addition of bis(trimethylsiloxy)phosphine to substituted vinyl- and divinylsilanes. The reaction proceeds regioselectively to form new silicon-containing ethyl phosphonites, the subsequent functionalization of which affords target different-structure tetraorganosilanes.

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References

  1. M. G. Voronkov, Advances in Organosilicon Chemistry, Mir, Moscow, 1985, 268.

    Google Scholar 

  2. Z. Rappoport, Y. Apeloig, S. Patai, The Chemistry of Organic Silicon Compounds, Wiley, Chichester, 1998. 2830.

    Book  Google Scholar 

  3. N. V. Ushakov, E. Sh. Finkelshtein, Russ. Chem. Rev., 2013, 82, 205; DOI: https://doi.org/10.1070/RC2013v082n03ABEH004323.

    Article  Google Scholar 

  4. M. G. Voronkov, V. M. Dyakov, Silatranes, Nauka, Novosibirsk, 1978, 208 (in Russian).

    Google Scholar 

  5. C. A. Black, J. W. Ucci, J. S. Vorpagel, M. C. Mauck, E. E. Fenlon, Bioorg. Med. Chem. Lett., 2002, 12, 3521; DOI: S0960-894X(02)00820-X.

    Article  CAS  PubMed  Google Scholar 

  6. G. A. Kutyrev, R. A. Cherkasov, Russ. Chem. Rev., 1984, 53, 971; DOI: https://doi.org/10.1070/RC1984v053n10ABEH003135.

    Article  Google Scholar 

  7. S. Weber, M. Glavic, B. Stöger, E. Pittenauer, M. Podewitz, L. F. Veiros, K. Kirchner, J. Am. Chem. Soc., 2021, 143, 17825; DOI: https://doi.org/10.1021/jacs.1c09175.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Z.-Lu Wang, F.-L. Zhang, J.-L. Xu, C.-C. Shan, M. Zhao, Y.-H. Xu, Org. Lett., 2020, 22, 7735; DOI: https://doi.org/10.1021/acs.orglett.0c02952.

    Article  CAS  PubMed  Google Scholar 

  9. L Zhang, M. Oestreich, Org. Lett., 2018, 20, 8061; DOI: https://doi.org/10.1021/acs.orglett.8b03714.

    Article  CAS  PubMed  Google Scholar 

  10. Z. Mo, J. Xiao, Y. Gao, L. Deng, J. Am. Chem. Soc., 2014, 136, 17414; DOI: https://doi.org/10.1021/ja510924v.

    Article  CAS  PubMed  Google Scholar 

  11. M. Nasim, L. I. Livantsova, D. P. Krutko, G. S. Zaitseva, J. Lorberth, M. Otto, J. Organomet. Chem., 1991, 402, 313; DOI: https://doi.org/10.1016/0022-328X(91)86245-L.

    Article  CAS  Google Scholar 

  12. A. V. Artem’ev, N. K. Gusarova, A. O. Korocheva, E. A. Matveeva, B. A. Trofimov, Russ. J. Gen. Chem., 2015, 85, 2416; DOI: https://doi.org/10.1134/S1070363215100321.

    Article  Google Scholar 

  13. V. P. Kukhar, H. R. Hudson, Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Wiley, New York, USA, 2000. 634.

    Google Scholar 

  14. S. C. Fields, Tetrahedron, 1999, 55, 12237; DOI: https://doi.org/10.1016/S0040-4020(99)00701-2.

    Article  CAS  Google Scholar 

  15. O. I. Kolodiazhnyi, Russ. Chem. Rev., 2006, 75, 227; DOI: https://doi.org/10.1070/RC2006v075n03ABEH001193.

    Article  CAS  Google Scholar 

  16. A. A. Prishchenko, R. S. Alekseyev, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. I. Terenin, V. S. Petrosyan, Russ. Chem. Bull., 2017, 66, 342; DOI: https://doi.org/10.1007/s11172-017-1737-4.

    Article  CAS  Google Scholar 

  17. A. A. Prishchenko, R. S. Alekseyev, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, J. Organomet. Chem., 2020, 912, 121177; DOI: https://doi.org/10.1016/j.jorganchem.2020.121177.

    Article  CAS  Google Scholar 

  18. A. A. Prishchenko, R. S. Alekseyev, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, J. Organomet. Chem., 2020, 917, 121286; DOI: https://doi.org/10.1016/j.jorganchem.2020.121286.

    Article  CAS  Google Scholar 

  19. A. A. Prishchenko, R. S. Alekseyev, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, J. Organomet. Chem., 2021, 949, 121950; DOI: https://doi.org/10.1016/j.jorganchem.2021.121950.

    Article  CAS  Google Scholar 

  20. A. A. Prishchenko, R. S. Alekseyev, O. P. Novikova, M. V. Livantsov, L. I. Livantsova, V. S. Petrosyan, J. Organomet. Chem., 2022, 957, 122143; DOI: https://doi.org/10.1016/j.jorganchem.2021.122143.

    Article  CAS  Google Scholar 

  21. A. A. Prishchenko, R. S. Alekseyev, O. P. Novikova, M. V. Livantsov, L. I. Livantsova, S. V. Baranin, Russ. Chem. Bull., 2022, 71, 1976; DOI:https://doi.org/10.1007/s11172-022-3616-x.

    Article  CAS  Google Scholar 

  22. A. A. Prishchenko, M. V. Livantsov, L. I. Livantsova, D. G. Polshchikov, S. N. Nikolaev, E. V. Grigoriev, Russ. J. Gen. Chem., 1999, 69, 151; DOI: 10.70-3632/99/6901-015.

    CAS  Google Scholar 

  23. A. A. Prishchenko, M. V. Livantsov, L. I. Livantsova, O. P. Novikova, S. N. Nikolaev, E. V. Grigoriev, Russ. J. Gen. Chem., 2003, 73, 492; DOI: 10.70-3632/03/7303-0492.

    Article  CAS  Google Scholar 

  24. L. Wozniak, J. Chojnowski, Tetrahedron, 1989, 45, 2465, DOI: https://doi.org/10.1016/S0040-4020(01)80083-1.

    Article  CAS  Google Scholar 

  25. V. D. Romanenko, M. V. Shevchuk, V. P. Kukhar, Curr. Org. Chem., 2011, 15, 2774; DOI: https://doi.org/10.2174/138527211796378505.

    Article  CAS  Google Scholar 

  26. Ya. A. Levin, E. I. Vorkunova, Homolytic Chemistry of Phosphorus, Nauka, Moscow, 1978, 318 (in Russian).

    Google Scholar 

  27. A. I. Rakhimov, Synthesis of Organophosphorus Compounds. Homolytic Reactions, Nauka, Moscow, 1985, 22 (in Russian)].

    Google Scholar 

  28. D. C. Nonhebel, J. M. Tedder, J. C. Walton, Radicals, Cambridge University Press, Cambridge, 1979, 200.

    Google Scholar 

  29. E. E. Nifantiev, Chemistry of Hydrophosphoryl Compounds., Nauka, Moscow, 1983, 264 (in Russian).

    Google Scholar 

  30. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2008, 19, 470; DOI: https://doi.org/10.1002/hc.20448.

    Article  CAS  Google Scholar 

  31. A. A. Prishchenko, M. V. Livantsov, V. S. Petrosyan, Russ. J. Gen. Chem., 1994, 64, 1316.

    CAS  Google Scholar 

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State Universitry, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    A. A. Prishchenko, M. V. Livantsov, O. P. Novikova & L. I. Livantsova

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

    S. V. Baranin & Yu. N. Bubnov

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Build. 1, 28 ul. Vavilova, 119334, Moscow, Russian Federation

    Yu. N. Bubnov

Authors
  1. A. A. Prishchenko
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  2. M. V. Livantsov
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  3. O. P. Novikova
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  4. L. I. Livantsova
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  5. S. V. Baranin
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  6. Yu. N. Bubnov
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Corresponding author

Correspondence to S. V. Baranin.

Additional information

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

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. 3, pp. 715–723, March, 2023.

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Prishchenko, A.A., Livantsov, M.V., Novikova, O.P. et al. Synthesis of functionalized phosphorus-containing tetraorganosilanes. Russ Chem Bull 72, 715–723 (2023). https://doi.org/10.1007/s11172-023-3836-9

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  • DOI: https://doi.org/10.1007/s11172-023-3836-9

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