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Free Radical Hydrophosphorylation of Fluoroalkyl Vinyl Ethers: Synthesis of Fluoroalkyl Phosphonates

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Abstract

An effective method for the synthesis of dialkyl [2-(polyfluoroalkoxy)ethyl]phosphonates by free radical hydrophosphorylation of fluoroalkyl vinyl ethers with dialkyl (H)-phosphonates was developed. The reaction proceeds in the presence of catalytic amounts of azabisisobutyric acid dinitrile (AIBN) (150°C, 2 h, portionwise addition of AIBN) to afford the target fluoroalkyl phosphonates in up to 85% isolated yield.

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REFERENCES

  1. Zhang, S.S., J. Power Sources, 2006, vol. 162, no. 2, p. 1379. https://doi.org/10.1016/j.jpowsour.2006.07.074

    Article  CAS  Google Scholar 

  2. Yoon, J.-G., Doo, S.-G., Hwang, S.-S., Park, K.-S., Gusarova, N.K., and Trofimov, B.A., US Patent 20070048622, 2007; C. A., 2007, vol. 146, p. 277725.

    Google Scholar 

  3. Han, S.-I., Shin, W.-C., Yu, J.-Y., Bae, T.-H., Lee, M.-H., Chernyshov, D., Tereshchenko, A., Shatunov, P., Trofimov, B.A., and Gusarova, N.K., US Patent 2012244445, 2012; C. A., 2012, vol. 157, p. 525496.

    Google Scholar 

  4. Chernyshov, D.V., Krachkovskiy, S.A., Kapylou, A.V., Bolshakov, I.A., Shin, W.C., and Ue, M., J. Electrochem. Soc., 2014, vol. 161, no. 4, p. A633. https://doi.org/10.1149/2.100404jes

  5. Haregewoin, A.M., Wotango, A.S., and Hwang, B.-J., Energy Environ. Sci., 2016, vol. 9, no. 6, p. 1955. https://doi.org/10.1039/c6ee00123h

    Article  CAS  Google Scholar 

  6. Aspern, N., Röser, S., Rad, B.R., Murmann, P., Streipert, B., Mönnighoff, X., Tillmann, S.D., Shevchuk, M., Stubbmann-Kazakova, O., Röschenthaler, G.-V., Nowak, S., Winter, M., and Cekic-Laskovic, I., J. Fluor. Chem., 2017, vol. 198, p. 24. https://doi.org/10.1016/j.jfluchem.2017.02.005

    Article  CAS  Google Scholar 

  7. Su, C.-C., He, M., Peebles, C., Zeng, L., Tornheim, A., Liao, C., Zhang, L., Wang, J., Wang, Y., and Zhang, Z., ACS Appl. Mater. Interfaces, 2017, vol. 9, p. 30686. https://doi.org/10.1021/acsami.7b0895

    Article  CAS  PubMed  Google Scholar 

  8. Zhang, H., Eshetu, G.G., Judez, X., Li, C., Rodriguez-Martínez, L.M., and Armand, M., Angew. Chem. Int. Ed., 2018, vol. 57, no. 46, p. 15002. https://doi.org/10.1002/anie.201712702

    Article  CAS  Google Scholar 

  9. Liu, K., Liu, Y., Lin, D., Pei, A., and Cui, Y., Sci. Adv., 2018, vol. 4, no. 6, p. 9820. https://doi.org/10.1126/sciadv.aas9820

    Article  CAS  Google Scholar 

  10. Romanenko, V.D. and Kukhar, V.P., Chem. Rev., 2006, vol. 106, no. 9, p. 3868. https://doi.org/10.1021/cr051000q

    Article  CAS  PubMed  Google Scholar 

  11. Turcheniuk, K.V., Kukhar, V.P., Röschenthaler, G.-V., Aceňa, J.L., Soloshonok, V.A., and Sorochinsky, A.E., RSC Adv., 2013, vol. 3, no. 19, p. 6693. https://doi.org/10.1039/C3RA22891F

    Article  CAS  Google Scholar 

  12. Liao, S., Fan, S.-Y., Liu, Q., Li, C.-K., Chen, J., Li, J.-L., Zhang, Z.-W., Zhang, Z.-Q., Zhong, B.-H., and Xie, J.-W., Arch. Pharm. Res., 2014, vol. 37, no. 11, p. 1416. https://doi.org/10.1007/s12272-013-0300-6

    Article  CAS  PubMed  Google Scholar 

  13. Mandadapu, S.R., Gunnam, M.R., Kankanamalage, A.C.G., Uy, R.A.Z., Alliston, K.R., Lushington, G.H., Kim, Y., Chang, K.-O., and Groutas, W.C., Bioorg. Med. Chem. Lett., 2013, vol. 23, no. 21, p. 5941. https://doi.org/10.1016/j.bmcl.2013.08.073

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Zhang, P., Guo, J., Meng, F., Sun, L., Zhong, B., and Zhao, Y., J. Pharm. Biomed. Anal., 2012, vol. 61, p. 70. https://doi.org/10.1016/j.jpba.2011.11.031

    Article  CAS  PubMed  Google Scholar 

  15. Wang, J.-Q., Fei, X., Gardner, T.A., Hutchins, G.D., and Zheng, Q.-H., Bioorg. Med. Chem., 2005, vol. 13, no. 2, p. 549. https://doi.org/10.1016/j.bmc.2004.10.007

    Article  CAS  PubMed  Google Scholar 

  16. Odinets, I.L., Artyushin, O.I., Goryunov, E.I., Lyssenko, K.A., Rybalkina, E.Yu., Kosilkin, I.V., Timofeeva, T.V., and Antipin, M.Yu., Heteroatom Chem., 2005, vol. 16, no. 6, p. 497. https://doi.org/10.1002/hc.20147

    Article  CAS  Google Scholar 

  17. Kim, C.U., Luh, B.Y., Misco, P.F., Bronson, J.J., Hitchcock, M.J.M., Ghazzouli, I., and Martin, J.C., J. Med. Chem., 1990, vol. 33, no. 4, p. 1207. https://doi.org/10.1021/jm00166a019

    Article  CAS  PubMed  Google Scholar 

  18. Pudovik, A.N., Konovalova, I.V., and Guryleva, A.A., Zh. Obshch. Khim., 1963, vol. 33, no. 9, p. 2924.

    CAS  Google Scholar 

  19. Nishiwaki, T., Tetrahedron, 1965, vol. 21, no. 11, p. 3043. https://doi.org/10.1016/S0040-4020(01)96923-6

    Article  CAS  Google Scholar 

  20. Nishiwaki, T., Tetrahedron, 1966, vol. 22, no. 2, p. 711. https://doi.org/10.1016/0040-4020(66)80042-X

    Article  CAS  Google Scholar 

  21. Trofimov, B.A., Atavin, A.S., Gavrilova, G.M., and Kalabin, G.A., Zh. Obshch. Khim., 1968, vol. 38, no. 10, p. 2344.

    CAS  Google Scholar 

  22. Jessop, C.M., Parsons, A.F., Routledge, A., and Irvine, D.J., Eur. J. Org. Chem., 2006, vol. 2006, no. 6, p. 1547. https://doi.org/10.1002/ejoc.200500907

    Article  CAS  Google Scholar 

  23. Trofimov, B.A., Khil’ko, M.Ya., Nedolya, N.A., Demanov, Yu.K., and Vyalykh, E.P., J. Org. Chem. USSR, 1982, vol. 18, no. 4, p. 647.

    Google Scholar 

  24. Yarmolenko, O.V., Yudina, A.V., and Ignatova, A.A., Elektrokhim. Energetika, 2016, vol. 16, no. 4, p. 155. https://doi.org/10.18500/1608-4039-2016-4-155-195

    Article  Google Scholar 

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Funding

This work was performed as part of the basic part of the governmental task (no. AAAA-A16116112510005-7) using the equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Russia

    L. A. Oparina, M. Ya. Khil’ko, N. A. Kolyvanov, N. K. Gusarova, N. A. Nedolya & B. A. Trofimov

  2. Irkutsk National Research Technical University, 664074, Irkutsk, Russia

    V. N. Saprygina

  3. Irkutsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Russia

    K. A. Apartsyn & V. V. Kireeva

Authors
  1. L. A. Oparina
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  2. M. Ya. Khil’ko
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  3. N. A. Kolyvanov
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  4. N. K. Gusarova
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  5. N. A. Nedolya
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  6. V. N. Saprygina
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  8. V. V. Kireeva
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  9. B. A. Trofimov
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Correspondence to B. A. Trofimov.

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Oparina, L.A., Khil’ko, M.Y., Kolyvanov, N.A. et al. Free Radical Hydrophosphorylation of Fluoroalkyl Vinyl Ethers: Synthesis of Fluoroalkyl Phosphonates. Russ J Gen Chem 90, 614–618 (2020). https://doi.org/10.1134/S107036322004009X

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  • DOI: https://doi.org/10.1134/S107036322004009X

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