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Synthesis of functionalized furan-containing phosphonous and phosphinic acids

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Abstract

A convenient synthesis of functionalized furan-containing phosphonous and phosphinic acids has been developed. The radical addition of bis(trimethylsiloxy)phosphine to 2-vinylfuran and trimethylsilyl 3-(2-furyl)acrylate proceeds regioselectively to afford new 2-furyl-substituted alkylphosphonites, the subsequent aminomethylation and carboxyethylation of which give various target phosphinic acids.

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References

  1. R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev., 2013, 113, 1499; DOI: https://doi.org/10.1021/cr300182k.

    Article  CAS  PubMed  Google Scholar 

  2. S. P. Teong, G. Yi Zhang, Green Chem., 2014, 16, 2015; DOI: https://doi.org/10.1039/C3GC42018C.

    Article  CAS  Google Scholar 

  3. X. Kong, Y. Zhu, Z. Fang, J. A. Kozinski, I. S. Butler, L. Xu, H. Song, X. Wei, Green Chem., 2018, 20, 3657; DOI: https://doi.org/10.1039/C8GC00234G.

    Article  CAS  Google Scholar 

  4. A. A. Rosatella, S. P. Simeonov, R. F. M. Frade, C. A. M. Afonso, Green Chem., 2011, 13, 754; DOI: https://doi.org/10.1039/C0GC00401D.

    Article  CAS  Google Scholar 

  5. F. A. Kucherov, L. V. Romashov, K. I. Galkin, V. P. Ananikov, ACS Sustain. Chem. Eng., 2018, 6, 8064; DOI: https://doi.org/10.1021/acssuschemeng.8b00971.

    Article  CAS  Google Scholar 

  6. G. M. Averochkin, E. G. Gordeev, M. K. Skorobogatko, F. A. Kucherov, V. P. Ananikov, ChemSusChem, 2021, 14, 3110; DOI: https://doi.org/10.1002/cssc.202100818.

    Article  CAS  PubMed  Google Scholar 

  7. F. A. Kucherov, L. V. Romashov, G. M. Averochkin, V. P. Ananikov, ACS Sustain. Chem. Eng., 2021, 9, 3011; DOI: https://doi.org/10.1021/acssuschemeng.0c09229.

    Article  CAS  Google Scholar 

  8. M. C. Dawson, D. C. Elliot, W. H. Elliot, K. M. Jones, Data for Biochemical Research, Clarendron Press, Oxford, 1986, 580.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. L. I. Livantsova, A. A. Prishchenko, M. V. Livantsov, S. N. Nikolaev, E. V. Grigoriev, Russ. J. Gen. Chem., 2000, 70, 1145.

    CAS  Google Scholar 

  14. A. A. Prishchenko, M. V. Livantsov, L. I. Livantsova, S. N. Nikolaev, E. V. Grigoriev, O. P. Novikova, Russ. J. Gen. Chem., 2000, 70, 1147.

    CAS  Google Scholar 

  15. A. A. Prishchenko, O. P. Novikova, M. V. Livantsov, L. I. Livantsova, S. V. Baranin, Yu. N Bubnov, Russ. Chem. Bull., 2023, 72, 715; DOI: https://doi.org/10.1007/s11172-023-3836-9.

    Article  CAS  Google Scholar 

  16. A. A. Prishchenko, O. P. Novikova, M. V. Livantsov, L. I. Livantsova, S. V. Baranin, Yu. N Bubnov, Russ. Chem. Bull., 2023, 72, 1088; DOI: https://doi.org/10.1007/s11172-023-3875-3.

    Article  CAS  Google Scholar 

  17. A. A. Prishchenko, R. S. Alekseyev, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Inorg. Chim. Acta, 2019, 484, 319; DOI: https://doi.org/10.1016/j.ica.2018.09.062.

    Article  CAS  Google Scholar 

  18. 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 

  19. 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 

  20. 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 

  21. 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 

  22. 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 

  23. 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 

  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. Nonhebel, J. Tedder, J. Walton, Radicals, Chembridge University Press, Chembridge, 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. Chemical Department, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskiye 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 Leninsky 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, 119991, 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.

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No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2138–2147, September, 2023.

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Prishchenko, A.A., Livantsov, M.V., Novikova, O.P. et al. Synthesis of functionalized furan-containing phosphonous and phosphinic acids. Russ Chem Bull 72, 2138–2147 (2023). https://doi.org/10.1007/s11172-023-4009-5

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  • DOI: https://doi.org/10.1007/s11172-023-4009-5

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