Oxidative Monofluorination of 1,4-Diiodo(or Dibromo)-2,3,5,6-tetramethylbenzenes in the System PbO₂—HF—Py—CH₂Cl₂

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Abstract

The oxidation of 1,4-diiodo-2,3,5,6-tetramethylbenzene (diiododurene) and 1,4-dibromo-2,3,5,6-tetramethylbenzene (dibromodurene) by lead dioxide PbO₂ in Olah reagent, hydrogen fluoride-pyridine mixture, with CH₂Cl₂ as a co-solvent at room temperature for 96 h results in the corresponding products of monofluorination of methyl group. This is the first example of using the oxidative system PbO₂—HF—Py—CH₂Cl₂ for side-chain monofluorination of methylated benzenes.

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About the authors

M. V. Kalyaev

Saint Petersburg State Forest Technical University; Saint Petersburg State University

Email: aleksvasil@mail.ru
Russian Federation, Institutsky per., 5, Saint Petersburg, 194021; Universitetskaya nab., 7/9, Saint Petersburg, 199034

D. S. Ryabukhin

Saint Petersburg State Forest Technical University; All-Russia Research Institute for Food Additives, V.M. Gorbatov Federal Research Center for Food Systems of RAS

Email: aleksvasil@mail.ru
ORCID iD: 0000-0001-5345-0038
Russian Federation, Institutsky per., 5, Saint Petersburg, 194021; Liteyniy pr., 55, Saint Petersburg, 191014

A. V. Vasilyev

Saint Petersburg State Forest Technical University; Saint Petersburg State University

Author for correspondence.
Email: aleksvasil@mail.ru
ORCID iD: 0000-0003-3628-1492
Russian Federation, Institutsky per., 5, Saint Petersburg, 194021; Universitetskaya nab., 7/9, Saint Petersburg, 199034

References

  1. Hiyama T. Organofluorine compounds. Chemistry and applications. Berlin: Springer, 2000.
  2. Chambers R. D. Fluorine in organic chemistry. Oxford, 2004.
  3. Kirsch P. Modern fluoroorganic chemistry: synthesis, reactivity, applications. Weinheim: Wiley-VCH, 2004.
  4. Uneyama K. Organofluorine chemistry. Oxford: Blackwell, 2006.
  5. Theodoridis G. Fluorine-containing agrochemicals: an overview of recent developments // Advances in Fluorine Science. Ed. A. Tressaud. Amsterdam: Elsevier. 2006, 2, 121–175.
  6. Begue J. P., Bonnet-Delpon D. Bioorganic and medicinal chemistry of fluorine. Hoboken: Wiley, 2008.
  7. Fluorine and health: molecular imaging, biomedical materials and pharmaceuticals. Eds. A. Tressaud, G. Haufe. Amsterdam: Elsevier, 2008.
  8. Fluorinated heterocyclic compounds: synthesis, chemistry, and applications. Ed. V.A. Petrov, Hoboken: Wiley, 2009.
  9. Fluorine in heterocyclic chemistry. Ed. V.G. Nenajdenko. Berlin: Springer, 2014.
  10. Prakash R.V. Organofluorine compounds in biology and medicine. Amsterdam: Elsevier, 2015.
  11. Fluorinated pharmaceuticals: advances in medicinal chemistry. Ed. A.D. Westwell. London: Future Science Ltd, 2015.
  12. Modern synthesis processes and reactivity of fluorinated compounds. Progress in fluorine science. Eds. H. Groult, F.R. Leroux, A. Tressaud. Amsterdam: Elsevier, 2017.
  13. Late-stage fluorination of bioactive molecules and biologically-relevant substrates. Ed. A. Postigo. Amsterdam: Elsevier, 2018.
  14. Champagne P.A., Desroches J., Hamel J.-D., Vandamme M., Paquin J.-F. Chem. Rev. 2015, 115, 9073–9174. doi: 10.1021/cr500706a
  15. Шаинян Б.А., Данилевич Ю.С., Григорьева А.А., Чувашев Ю.А. ЖОрХ. 2003, 39, 1651–1656. [Shainyan B.A., Danilevich Yu.S., Grigor’eva A.A., Chuvashev Yu.A. Russ. J. Org. Chem. 2003, 39, 1581–1586.] doi: 10.1023/B:RUJO.0000013131.19936.5e
  16. Шаинян Б.А., Данилевич Ю.С., Григорьева А.А., Чувашев Ю.А. ЖОрХ. 2004, 40, 544–548. [Shainyan B.A., Danilevich Yu.S., Grigor’eva A.A., Chuvashev Yu.A., Russ. J. Org. Chem. 2004, 40, 513–517.] doi: 10.1023/B:RUJO.0000036072.78258.c2
  17. Шаинян Б.А., Данилевич Ю.С. ЖОрХ. 2006, 42, 231–235. [Shainyan B.A., Danilevich Yu.S., Russ. J. Org. Chem. 2006, 42, 214–219.] doi: 10.1134/S1070428002120096
  18. Polczynski P., Jurczakowski R., Grzelak A., Goreshnik E., Mazej Z., Grochala W. Chem. Eur. J. 2019, 25, 4927–4930. doi: 10.1002/chem.201806274
  19. Polczynski P., Jurczakowski R., Mazej Z., Dobrzycki L., Grzelak A., Grochala W. Eur. J. Inorg. Chem. 2020, 33 3151–3157. doi: 10.1002/ejic.202000363
  20. A.E. Feiring, J. Fluor. Chem. 1977, 10, 375–386. doi: 10.1016/S0022-1139(00)82143-0
  21. A.E. Feiring, J. Org. Chem. 1979, 44, 1252–1254. doi: 10.1021/jo01322a013
  22. Щукин А.О., Васильев А.В., Фукин Г.К., Руденко А.П. ЖОрХ. 2007, 43, 1455–1459. [Shchukin A.O., Vasilyev A.V., Fukin G.K., Rudenko A.P. Russ. J. Org. Chem. 2007, 43, 1446–1450.] doi: 10.1134/S1070428007100065
  23. G.A. Olah, J. T. Welch, Y.D. Vankar, M. Nojima, I. Kerekes, J.A. Olah, J. Org. Chem. 1979, 44, 3872–3881. doi: 10.1021/jo01336a027
  24. Chen C., Chien C.-T., Su C.-H., J. Fluor. Chem. 2002, 115, 75–77. doi: 10.1016/S0022-1139(02)00004-0
  25. Ranjith J., Rajesh N., Sridhar B., Krishna P.R. Org. Biomol. Chem. 2016, 14, 10074–10079. doi: 10.1039/c6ob01752e
  26. Hiraoka T., Yano S., Hara S. Synthesis. 2016, 48, 1353–1358. doi: 10.1055/s-0035-1561374
  27. Marzijarani N.S., Snead D.R., McMullen J.P., Leve-son F., Weisel M., Varsolona R.J., Lam Y., Liu Z., Naber J.R. Org. Process Res. Dev. 2019, 23, 1522–1528. doi: 10.1021/acs.oprd.9b00178
  28. Golushko A.A., Dar’in D.V., Kantin G.P., Guranova N., Vasilyev A.V., Krasavin M.Yu. Synthesis. 2019, 51, 3815–3824. doi: 10.1055/s-0037-1611882
  29. Vasilyev A.V. Mini-Rev. Org. Chem. 2017, 14, 204–206. doi: 10.2174/1570193X14666170208101802
  30. Санджиева М.А., Арямова Е.С., Сухаржевский С.М., Гриненко Е.В., Васильев А.В. ЖОрХ. 2017, 54, 393–398. [Sandzhieva M.A., Aryamova E.S., Sukharzhevskii S.M., Grinenko E.V., Vasilyev A.V. Russ. J. Org. Chem. 2018, 54, 393–398.] doi: 10.1134/S1070428018030053
  31. Miyaura N. Cross-Coupling Reactionс: A Practical Guide. Berlin–Heidelberg: Springer, 2002.
  32. Niсhihara Y. Applied Cross-Coupling Reactions. Berlin–Heidelberg: Springer, 2013.
  33. De Meijere A., Diederich F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. Weinheim: Wiley-VCH, 2004.
  34. Руденко А.П. ЖОрХ. 1994, 30, 1847–1881. [Ruden-ko A.P. Russ. J. Org. Chem. 1994, 30, 1802–1833.]

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