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Selective fluorination of pyridine and its derivatives in the presence of high-oxidation-state transition metals

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Abstract

The oxidative fluorination of pyridine and 4-ethylpyridine under chemical and electro-chemical conditions in the presence of transition metal (high-oxidation-state nickel, cobalt, and silver) salts was studied. The chemical fluorination affords 2-fluoropyridine in all cases, while the electrochemical fluorination results in 2-fluoroor 3-fluoropyridine depending on the catalyst used.

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References

  1. F. Dollé, Curr. Pharm. Des., 2005, 11, 3221.

    Article  Google Scholar 

  2. J. A. McCarron, V. W. Pike, C. Halldin, J. Sandell, J. Sóvágó, B. Gulyas, Z. Cselényi, H. V. Wikström, S. Marchais-Oberwinkler, B. Nowicki, F. Dollé, L. Farde, Mol. Imaging Biol. 2004, 6, 17

    Article  Google Scholar 

  3. V. W. Pike, Trends Pharmacol. Sci., 2009, 30, 431.

    Article  CAS  Google Scholar 

  4. V. A. Petrov, Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications; John Wiley & Sons, Hoboken, 2009, 533 p.

    Book  Google Scholar 

  5. P. S. Fier, J. F. Hartwig, Science, 2013, 342, 956

    Article  CAS  Google Scholar 

  6. P. S. Fier, J. F. Hartwig, J. Am. Chem. Soc., 2014, 136, 10139.

    Article  CAS  Google Scholar 

  7. H. Sun, S. G. DiMagno, Angew. Chem., Int. Ed., 2006, 45, 2720

    Article  CAS  Google Scholar 

  8. T. Fukuhara, N. Yoneda, A. Suzuki, J. Fluorine Chem., 1988, 38, 435

  9. S. D. Kuduk, R. M. DiPardo, M. G. Bock, Org.Lett., 2005, 7, 577.

    Article  CAS  Google Scholar 

  10. L. Dolci, F. Dollé, S. Jubeau, F. Vaufrey, J. Crouzel, J. Labelled Compd. Radiopharm., 1999, 42, 975

    Article  CAS  Google Scholar 

  11. M. Karramkam, F. Hinnen, F. Vaufrey, F. Dollé, J. Labelled Compd. Radiopharm., 2003, 46, 979.

    Article  CAS  Google Scholar 

  12. D. E. Olberg, J. M. Arukwe, D. Grace, O. K. Hjelstuen, M. Solbakken, G. M. Kindberg, A. Cuthbertson, J. Med. Chem., 2010, 53, 1732

    Article  CAS  Google Scholar 

  13. F. Dollé, L. Dolci, H. Valette, F. Hinnen, F. Vaufrey, I. Guenther, C. Fuseau, C. Coulon, M. Bottlaender, C. Crouzel, J. Med. Chem., 1999, 42, 2251

    Article  Google Scholar 

  14. Y.-S. Ding, N. Liu, T. Wang, J. Marecek, V. Garza, I. Ojima, J. S. Fowler, Nucl. Med. Biol., 2000, 27, 381.

    Article  CAS  Google Scholar 

  15. J. A. Bull, J. J. Mousseau, G. Pelletier, A. B. Charette, Chem. Rev., 2012, 112, 2642

    Article  CAS  Google Scholar 

  16. C. Liu, J. Luo, L. Xu, Z. Huo, ARKIVOC, 2013, Part (i), 154

    Google Scholar 

  17. J. J. Yin, B. P. Xiang, M. A. Huffman, C. E. Raab, I. W. Davies, J. Org. Chem., 2007, 72, 4554

  18. J. M. Keith, J. Org. Chem., 2008, 73, 327

    Article  CAS  Google Scholar 

  19. J. M. Keith, J. Org. Chem., 2010, 75, 2722

    Article  CAS  Google Scholar 

  20. A. T. Londregan, S. Jennings, L. Q. Wei, Org. Lett., 2010, 12, 5254

    Article  CAS  Google Scholar 

  21. A. T. Londregan, S. Jennings, L. Q. Wei, Org. Lett., 2011, 13, 1840

    Article  CAS  Google Scholar 

  22. S. E. Wengryniuk, A. Weickgenannt, C. Reiher, N. A. Strotman, K. Chen, M. D. Eastgate, P. S. Baran, Org. Lett., 2013, 15, 792

    Article  CAS  Google Scholar 

  23. R. P. Farrell, M. V. Silva Elipe, M. D. Bartberger, J. S. Tedrow, F. Vounatsos, Org. Lett., 2013, 15, 168.

    Article  CAS  Google Scholar 

  24. Pat. EU EP0619307, 1994; https://www.google.com/patents/EP0619307A1?cl=en&hl=ru.

  25. E. Rivadeneira, K. Jelich, Eur. Pat. EP 556683, 1993; https://www.google.com/patents/EP0556683A1?cl=en

  26. E. Rivadeneira, K. Jelich, Pat. US 5502194, 1996; http://www.google.com/patents/US5502194

  27. A. Johansson, T. Svensson, Pat. WO/2001/070730, 2001; http://www.google.com/patents/WO2001070730A1?cl=en.

  28. H. Xiong, A. T. Hoye, K.-H. Fan, X. Li, J. Clemens, C. L. Horchler, N. C. Lim, G. Attardo, Org. Lett., 2015, 17, 3726.

    Article  CAS  Google Scholar 

  29. J. R. Ballinger, F. W. Teare, B. M. Bowen, E. S. Garnett, Electrochim. Acta, 1985, 30, 1075.

    Article  CAS  Google Scholar 

  30. A. Lin, C. B. Huehls, J. Yang, Org. Chem. Front., 2014, 1, 434

    Article  CAS  Google Scholar 

  31. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem., Int. Ed., 2013, 52, 8214

    Article  CAS  Google Scholar 

  32. N. Bartlett, R. D. Chambers, A. J. Roche, R. C. H. Spink, L. Chaconb, J. M. Whalen, Chem. Commun., 1996, 1049

    Google Scholar 

  33. B. Zenva, K. Lutor, L. Chacon, M. Fele-Beuermann, J. Allman, C. Shen, N. Bartlett, J. Am. Chem. Soc., 1995, 117, 10025

  34. N. Bartlett, R. D. Chambers, A. J. Roche, R. C. H. Spink, L. Chacon, J. M. Whalen, J. Chem. Soc., Chem. Commun., 1996, 1049

    Google Scholar 

  35. S.-J. Lou, D.-Q. Xu, A.-B. Xia, Y.-F. Wang, Y.-K. Liu, X.-H. Du, Z.-Y. Xu, Chem. Commun., 2013, 49, 6218.

    Article  CAS  Google Scholar 

  36. P. Sartori, N. Ignat’ev, J. Fluorine Chem., 1998, 87, 157

    Article  CAS  Google Scholar 

  37. F. G. Drakesmith, in Topics in Current Chemistry, Springer, Berlin, 1997, Vol. 193, p. 197.

  38. M. N. Khrizanforov, D. M. Arkhipova, R. P. Shekurov, T. P. Gerasimova, V. V. Ermolaev, D. R. Islamov, V. A. Miluykov, O. N. Kataeva, V. V. Khrizanforova, O. G. Sinyashin, Y. H. Budnikova., J. Solid State Electrochem., 2015, 19, 2883.

    Article  CAS  Google Scholar 

  39. N. Bartlett, R. Chambers, A. J. Roche, R. C. H. Spink, L. Chacyn, J. M. Whalen, Chem. Commun., 1996, 1049.

    Google Scholar 

  40. J. Holzbock, W. Sawodny, L. Walz, Z. Kristallogr., 1997, 212, 115.

    CAS  Google Scholar 

  41. J. Holzbock, W. Sawodny, U. Thewalt, Z. Anorg. Allg. Chem., 2000, 626, 2563.

    Article  CAS  Google Scholar 

  42. M. Ye, G.-L. Gao, J.-Q. Yu, J. Am. Chem. Soc., 2011, 133, 6964.

    Article  CAS  Google Scholar 

  43. J. A. Joule, R. Mills, Heterocyclic Chemistry, 4th ed., Blackwell Sci., Oxford, 2000, 589 pp.

    Google Scholar 

  44. T. Umemoto, K. Harasawa, G. Tomizawa, J. Fluorine Chem., 1991, 53, 369

    Article  CAS  Google Scholar 

  45. T. Umemoto, K. Harasawa, G. Tomizawa, K. Kawada, K. Tomita, Bull. Chem. Soc. Jpn., 1991, 64, 1081.

    Article  CAS  Google Scholar 

  46. A. Y. Denisov, V. I. Mamatyuk, O. P. Shkuro, Magn. Reson. Chem., 1985, 23, 482.

    Article  CAS  Google Scholar 

  47. P. Tang, W. Wang, T. Ritter, J. Am. Chem. Soc., 2011, 133, 11482.

    Article  CAS  Google Scholar 

  48. R. D. Chambers, M. Parsons, G. Sandford, Ch. J. Skinner, M. J. Atherton, J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803.

    Google Scholar 

  49. T. Furuya, T. Ritter, Org. Lett., 2009, 11, 2860.

    Article  CAS  Google Scholar 

  50. Eur. Pat. Appl. EP 1595881 (A1); https://worldwide. espacenet.com.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Arbuzova, 420088, Kazan, Russian Federation

    T. V. Gryaznova, V. V. Khrizanforova, K. V. Kholin, M. N. Khrizanforov & Yu. H. Budnikova

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  1. T. V. Gryaznova
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  2. V. V. Khrizanforova
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  3. K. V. Kholin
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  4. M. N. Khrizanforov
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  5. Yu. H. Budnikova
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Correspondence to T. V. Gryaznova.

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Based on the materials of the International Conference “Organometallic and Coordination Chemistry. Problems and Advances” (VI Razuvaev Readings) (September 18–23, 2015, Nizhny Novgorod, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1798–1804, July, 2016.

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Gryaznova, T.V., Khrizanforova, V.V., Kholin, K.V. et al. Selective fluorination of pyridine and its derivatives in the presence of high-oxidation-state transition metals. Russ Chem Bull 65, 1798–1804 (2016). https://doi.org/10.1007/s11172-016-1513-x

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  • DOI: https://doi.org/10.1007/s11172-016-1513-x

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