Mechanochemical fluorination of naproxen and its salts with F-TEDA-BF4

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Abstract

The mechanochemical fluorination of naproxen and its salts (Li, Na and K) using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, F-TEDA-BF4) has been studied. The reaction of naproxen with an excess of Selectfluor gives 2-(5,5-difluoro-6-oxo-5,6-dihydronaphthalene-2-yl)propionic acid in high yield. The use of a small amount of Al2O3, SiO2, M2CO3 (M = Na, K, Rb, Cs), ionic liquids (ILs), crown ethers, and N-bases enhances the rate of reaction of naproxen with Selectfluor and increases the proportion of the monofluorination product compared to the difluorination product.

About the authors

G. I. Borodkin

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

Email: gibor@nioch.nsc.ru

I. R. Elanov

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

V. G. Shubin

Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences

References

  1. Ilyas S., Jilani K., Sikandar M., Siddiq S., Riaz M., Naveed A., Bibi I., Nawaz H., Irfan M., Asghar A. Dose Response Inter. J. 2020, 18, 1-6. doi: 10.1177/1559325819899259
  2. Saji R.S., Prasana J.C., Muthu S., George J., Kuruvilla T.K., Raajaraman B.R. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2020, 226, 117614. doi: 10.1016/j.saa.2019.117614
  3. Mohammed A., Yarla N.S., Madka V., Rao C.V. Int. J. Mol. Sci. 2018, 19, 2332-2349. doi: 10.3390/ijms19082332
  4. Hui D.S., Lee N., Chan P.K., Beigel J.H. Antivir. Res. 2018, 150, 202-216. doi: 10.1016/j.antiviral.2018.01.002
  5. Lejal N., Tarus B., Bouguyon E., Chenavas S., Bertho N., Delmas B., Ruigrok R.W.H., Primo C.D., Slama-Schwok A. Antimicrob. Agents Chemother. 2013, 57, 2231-2242. doi: 10.1128/AAC.02335-12
  6. Yerien D.E., Bonesi S, Postigo A. Org. Biomol. Chem. 2016, 14, 8398-8427. doi: 10.1039/c6ob00764c
  7. Zaikin P.A., Borodkin G.I. Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates. Ed. A. Postigo. Amsterdam: Elsevier. 2019, 105-135.
  8. Gillis E.P., Eastman K.J., Hill M.D., Donnelly D.J., Meanwell N.A. J. Med. Chem. 2015, 58, 8315-8359. doi: 10.1021/acs.jmedchem.5b00258
  9. Alvarez F.S. Пат. 3637767A (1972). США
  10. Schlosser M., Michel D., Guo Z.-w., Sih C.J. Tetrahedron. 1996, 52, 8257-8262. doi: 10.1016/0040-4020(96)00411-5
  11. Goj O., Kotila S., Haufe G. Tetrahedron. 1996, 52, 12761-12774. doi: 10.1016/0040-4020(96)00758-2
  12. Fujisawa H.,Fujiwara T., Takeuchi Y., Omata K. Chem. Pharm. Bull. 2005, 53, 524-528. doi: 10.1248/cpb.53.524
  13. Borodkin G.I., Elanov I.R., Gatilov Yu.V., Shubin V.G. J. Fluor. Chem. 2019, 228, 109412. doi: 10.1016/j.jfluchem.2019.109412
  14. Tan D., Friščić T. Eur. J. Org. Chem. 2018, 18-33. doi: 10.1002/ejoc.201700961
  15. Бородкин Г.И., Шубин В.Г. ЖОрХ. 2021, 57, 1209-1242.
  16. Borodkin G.I., Shubin V.G. Russ. J. Org. Chem. 2021, 57, 1369-1397. doi: 10.1134/S1070428021090013
  17. Zaikin P.A., Dyan Ok Ton, Elanov I.R., Borodkin G.I. Molecules. 2021, 26, 5756. doi: 10.3390/molecules26195756
  18. Gomollón-Bel F. Chem. Int. 2019, 41, 12-17. doi: 10.1515/ci-2019-0203
  19. Ionic Liquids in Synthesis. Eds. P. Wasserscheid, T. Welton. Weinheim: Wiley, 2008. doi: 10.1002/9783527621194
  20. Sandhu S., Sandhu J.S. Green Chem. Lett. Rev. 2011, 4, 289-310. doi: 10.1080/17518253.2011.572294
  21. Maton C., Vos N.D., Stevens C.V. Chem. Soc. Rev. 2013, 42, 5963-5977. doi: 10.1039/c3cs60071h
  22. Бородкин Г.И., Шубин В.Г. ЖОрХ. 2006, 42, 1761-1783.
  23. Borodkin G.I., Shubin V.G. Russ. J. Org. Chem. 2006, 42, 1745-1770. doi: 10.1134/S1070428006120013
  24. Laali K.K., Borodkin G.I. J. Chem. Soc., Perkin Trans. 2. 2002, 953-957. doi: 10.1039/b111725d
  25. Heravi M.R.P. J. Fluor. Chem. 2008, 129, 217-221. doi: 10.1016/j.jfluchem.2007.11.006
  26. Pavlinac J., Zupan M., Laali K.K., Stavber S. Tetrahedron. 2009, 65, 5625-5662. doi: 10.1016/j.tet.2009.04.092
  27. Bogautdinov R.P., Fidarov A.F., Morozkina S.N., Zolotarev A.A., Starova G.L., Selivanov S.I., Shavva A.G. J. Fluor. Chem. 2014, 168, 218-222. doi: 10.1016/j.jfluchem.2014.09.030
  28. Laali K.K. Arkivoc. 2016, i, 50-171. doi: 10.3998/ark.5550190.p009.490
  29. Gu Q., Vessally E. RSC Adv. 2020, 10, 6756-16768. doi: 10.1039/D0RA00324G
  30. Timofeeva D.S., Ofial A.R., Mayr H. J. Am. Chem. Soc. 2018, 140, 11474-11486. doi: 10.1021/jacs.8b07147
  31. Zaikin P.A., Dyan Ok Ton, Evtushok D.V., Usoltsev A.N., Borodkin G.I., Karpova E.V., Shubin V.G. Eur. J. Org. Chem. 2017, 2469-2474. doi: 10.1002/ejoc.201700179

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