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Electrophilic Fluorination of Heterocyclic Compounds with NF Reagents in Unconventional Media

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Chemistry of Heterocyclic Compounds Aims and scope

Data on the electrophilic fluorination of heterocyclic compounds with NF reagents in unconventional media (ionic liquids, water and aqueous solutions, solvent-free media) were summarized and analyzed. The effect of the medium and the problem of selectivity were particularly considered.

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References

  1. Gupta, S. P. Lett. Drug Des. Discovery 2019, 16, 1089.

    Article  CAS  Google Scholar 

  2. Mei, H.; Han, J.; White, S.; Graham, D. J.; Izawa, K.; Sato, T.; Fustero, S.; Meanwell, N. A.; Soloshonok, V. A. Chem.–Eur. J. 2020, 26, 11349.

  3. Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J. L.; Soloshonok, V. F.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.

    Article  CAS  PubMed  Google Scholar 

  4. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.

    Article  CAS  PubMed  Google Scholar 

  5. Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem. 2010, 131, 1267.

    Article  CAS  Google Scholar 

  6. Dhiman, P.; Arora, N.; Thanikachalam, P. V.; Monga, V. Bioorg. Chem. 2019, 92, 103291.

    Article  CAS  PubMed  Google Scholar 

  7. Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D. M.; Santi, C.; Ruzziconi, R.; Soloshonok, V. A. Chem.–Eur. J. 2019, 25, 11797.

  8. Bremer, M.; Kirsch, P.; Klasen-Memmer, M.; Tarumi, K. Angew. Chem., Int. Ed. 2013, 52, 8880.

    Article  CAS  Google Scholar 

  9. Yerien, D. E.; Bonesi, S.; Postigo, A. Org. Biomol. Chem. 2016, 14, 8398.

    Article  CAS  PubMed  Google Scholar 

  10. Squeo, B. M.; Gregoriou, V. G.; Avgeropoulos, A.; Baysec, S.; Allard, S.; Scherf, U.; Chochos, C. L. Prog. Polym. Sci. 2017, 71, 26.

    Article  CAS  Google Scholar 

  11. Mykhailiuk, P. K. Chem. Rev. 2021, 121, 1670.

    Article  CAS  PubMed  Google Scholar 

  12. Rozatian, N.; Hodgson, D. R. W. Chem. Commun. 2021, 57, 683.

    Article  CAS  Google Scholar 

  13. Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719.

    Article  CAS  PubMed  Google Scholar 

  14. Kirsch, P. J. Fluorine Chem. 2015, 177, 29.

    Article  CAS  Google Scholar 

  15. Vincent, J.-M. Chem. Commun. 2012, 48, 11382.

    Article  CAS  Google Scholar 

  16. Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem. 2016, 24, 317.

    Article  CAS  PubMed  Google Scholar 

  17. Postigo, A. In Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates; Postigo, A., Ed.; Elsevier: Amsterdam, 2019, p. 1.

  18. Zaikin, P. A.; Borodkin, G. I. In Late-Stage Fluorination of Bioactive Molecules and Biologically-Relevant Substrates; Postigo, A., Ed.; Elsevier: Amsterdam, 2019, p. 105.

  19. Gillis, E. P.; Eastmann, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.

    Article  CAS  PubMed  Google Scholar 

  20. Nosova, E. V.; Lipunova, G. N.; Charushin, V. N.; Chupakhin, O. N. J. Fluorine Chem. 2018, 212, 51.

    Article  CAS  Google Scholar 

  21. Inoue, M.; Sumii, Y.; Shibata, N. ACS Omega 2020, 5, 10633.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  Google Scholar 

  23. Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.

    Article  CAS  PubMed  Google Scholar 

  24. Kohlhepp, S. V.; Gulder, T. Chem. Soc. Rev. 2016, 45, 6270.

    Article  CAS  PubMed  Google Scholar 

  25. Han, Z.-Z.; Zhang, C.-P. Adv. Synth. Catal. 2020, 362, 4256.

    Article  CAS  Google Scholar 

  26. Borodkin, G. I.; Shubin, V. G. Russ. Chem. Rev. 2010, 79, 259.

    Article  CAS  Google Scholar 

  27. Rozen, S. In Advances in Organic Synthesis: Modern Organofluorine Chemistry – Synthetic Aspects; Atta-ur- Rahman, K. K.; Laali, Eds.; Bentham, 2006, Vol. 2, p. 3.

  28. Sandford, G. J. Fluorine Chem. 2007, 128, 90.

    Article  CAS  Google Scholar 

  29. Tius, M. A. Tetrahedron 1995, 24, 6605.

    Article  Google Scholar 

  30. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.

    Article  CAS  Google Scholar 

  31. Baudoux, J.; Cahard, D. In Organic Reactions; Overman, L. E., Ed.; J. Wiley and Sons, 2007, vol. 69, p. 347.

  32. Gu, Q.; Vessally, E. RSC Adv. 2020, 10, 16756.

    Article  CAS  Google Scholar 

  33. Borodkin, G. I.; Shubin, V. G. Russ. J. Org. Chem. 2021, 57, 1369.

    Article  CAS  Google Scholar 

  34. Borodkin, G. I.; Shubin, V. G. Russ. J. Org. Chem. 2006, 42, 1745.

    Article  CAS  Google Scholar 

  35. Pavlinac, J.; Zupan, M.; Laali, K. K.; Stavber, S. Tetrahedron 2009, 65, 5625.

    Article  CAS  Google Scholar 

  36. Laali, K. K.; Borodkin, G. I. J. Chem. Soc., Perkin Trans. 2 2002, 953.

  37. Baudoux, J.; Salit, A.-F. Cahard, D; Plaquevent, J.-C. Tetrahedron Lett. 2002, 43, 6573.

  38. Reddy, A. S; Laali, K. K. Tetrahedron Lett. 2015, 56, 5495.

  39. Borodkin, G. I.; Elanov, I. R.; Gatilov, Y. V.; Shubin, V. G. RSC Adv. 2016, 6, 60556.

    Article  CAS  Google Scholar 

  40. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302.

    Article  CAS  PubMed  Google Scholar 

  41. Gawande, M. B.; Bonifácio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 5522.

    Article  CAS  PubMed  Google Scholar 

  42. Yang, L.; Dong, T.; Revankar, H. M.; Zhang, C.-P. Green Chem. 2017, 19, 3951.

    Article  CAS  Google Scholar 

  43. Cortes-Clerget, M.; Yu, J.; Kincaid, J. R. A.; Walde, P.; Gallou, F.; Lipshutz, B. H. Chem. Sci. 2021, 12, 4237.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  44. Kitanosono, T.; Kobayashi, S. Chem.–Eur. J. 2020, 26, 9408.

  45. Lipshutz, B. H.; Ghorai, S.; Cortes-Clerget, M. Chem.–Eur. J. 2018, 24, 6672.

  46. Dunn, P. J. Chem. Soc. Rev. 2012, 41, 1452.

    Article  CAS  PubMed  Google Scholar 

  47. Fields, S. C.; Lo, W. C.; Brewster, W. K.; Lowe, C. T. Tetrahedron Lett. 2010, 51, 79.

    Article  CAS  Google Scholar 

  48. Borodkin, G. I.; Elanov, I. R.; Shubin, V. G. Russ. J. Org. Chem. 2014, 50, 1064.

    Article  CAS  Google Scholar 

  49. Borodkin, G. I.; Elanov, I. R.; Shubin, V. G. Russ. J. Org. Chem. 2015, 51, 1003.

    Article  CAS  Google Scholar 

  50. Ghosh, P.; Hajra, A. J. Org. Chem. 2021, 86, 10883.

    Article  CAS  PubMed  Google Scholar 

  51. Kalari, S.; Balasubramanian, S.; Rode, H. B. Tetrahedron Lett. 2021, 71, 153028.

    Article  CAS  Google Scholar 

  52. Stavber, G.; Stavber, S. Adv. Synth. Catal. 2010, 352, 2838.

    Article  CAS  Google Scholar 

  53. Li, J.; Li, Y.-L.; Jin, N.; Ma, A.-L.; Huang, Y.-N.; Deng, J. Adv. Synth. Catal. 2015, 357, 2474.

    Article  CAS  Google Scholar 

  54. Phae-nok, S.; Pohmakotr, M.; Kuhakarn, C.; Reutrakul, V.; Soorukram, D. Eur. J. Org. Chem. 2019, 4710.

  55. Liu, J.; Chan, J.; Bryant, C. M.; Duspara, P. A.; Lee, E. E.; Powell, D.; Yang, H.; Liu, Z.; Walpole, C.; Roberts, E.; Batey, R. A. Tetrahedron Lett. 2012, 53, 2971.

    Article  CAS  Google Scholar 

  56. Bao, X.; Wei, S.; Zou, L.; Song, Y.; Qu, J.; Wang, B. Tetrahedron: Asymmetry 2016, 27, 436.

    Article  CAS  Google Scholar 

  57. Reddy, N. S.; Kumar, N. R.; Swaroop, D. R.; Punna, N.; Dev, G. J.; Babu, N. J.; Narsaiah, B. Eur. J. Org. Chem. 2019, 2409.

  58. Seki, T.; Fujiwara, T.; Takeuchi, Y. J. Fluorine Chem. 2011, 132, 181.

    Article  CAS  Google Scholar 

  59. Lin, R.; Ding, S.; Shi, Z.; Jiao, N. Org. Lett. 2011, 13, 4498.

    Article  CAS  PubMed  Google Scholar 

  60. Liu, N.; Tian, Q.-P.; Yang, Q.; Yang, S.-D. Synlett 2016, 2621.

  61. Sun, X.; Zhao, X.-J.; Wu, B. Asian J. Org. Chem. 2017, 6, 690.

    CAS  Google Scholar 

  62. Liu, P.; Gao, Y.; Gu, W.; Shen, Z.; Sun, P. J. Org. Chem. 2015, 80, 11559.

    Article  CAS  PubMed  Google Scholar 

  63. Zhou, G.; Tian, Y.; Zhao, X.; Dan, W. Org. Lett. 2018, 20, 4858.

    Article  CAS  PubMed  Google Scholar 

  64. Zhao, M.; Cai, J.; Zhao, X. Org. Chem. Front. 2019, 6, 426.

    Article  CAS  Google Scholar 

  65. Tian, Y.; Zhou, G.; Zhao, X.; Dan, W. Acta Chim. Sinica 2018, 76, 962.

    Article  CAS  Google Scholar 

  66. Roque, J. B.; Kuroda, Y.; Gottemann, L. T.; Sarpong, R. Science 2018, 361, 171.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  67. Roque, J. B.; Sarpong, R.; Musaev, D. G. J. Am. Chem. Soc. 2021, 143, 3889.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. Liu, Z.; Yoshihara, A.; Kelly, C.; Heap, J. T.; Marqvorsen, M. H. S.; Jenkinson, S. F.; Wormald, M. R.; Otero, J. M.; Estévez, A.; Kato, A.; Fleet, G. W. J.; Estévez, R. J.; Izumori, K. Chem.– Eur. J. 2016, 22, 12557.

  69. Reeve, P. A. P.; Grabowska, U.; Oden, L. S.; Wiktelius, D.; Wangsell, F.; Jackson, R. F. W. ACS Omega 2019, 4, 10854.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  70. Heggelund, A.; Undheim, K. Synth. Commun. 2009, 39, 1903.

    Google Scholar 

  71. Thornbury, R. T.; Saini, V.; Fernandes, T. A.; Santiago, C. B.; Talbot, E. P. A.; Sigman, M. S.; McKenna, J. M.; Toste, F. D. Chem. Sci. 2017, 8, 2890.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  72. Zhu, J.-S.; McCormick, N. E.; Timmons, S. C.; Jakeman, D. L. J. Org. Chem. 2016, 81, 8816.

    Article  CAS  PubMed  Google Scholar 

  73. Francisco, C. G.; González, C. C.; Kennedy, A. R.; Paz, N. R.; Suárez, E. Chem.–Eur. J. 2008, 14, 6704.

  74. Wang, M.; Liu, X.; Zhou, L.; Zhu, J.; Sun, X. Org. Biomol. Chem. 2015, 13, 3190.

    Article  CAS  PubMed  Google Scholar 

  75. Punirun, T.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. J. Org. Chem. 2015, 80, 7946.

    Article  CAS  PubMed  Google Scholar 

  76. Xu, Y.-S.; Tang, Y.; Feng, H.-J.; Liu, J.-T.; Hsung, R. P. Org. Lett. 2015, 17, 572.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  77. Yang, Q.; Mao, L.-L.; Yang, B.; Yang, S.-D. Org. Lett. 2014, 16, 3460.

    Article  CAS  PubMed  Google Scholar 

  78. Li, Z.; Zhang, C.; Zhu, L.; Liu, C.; Li, C. Org. Chem. Front. 2014, 1, 100.

    Article  CAS  Google Scholar 

  79. Thonhofer, M.; Santana, A. G.; Fischer, R.; Gomez, A. T.; Saf, R.; Schalli, M.; Stutz, A. E.; Withers, S. G. Carbohydr. Res. 2016, 420, 6.

    Article  CAS  PubMed  Google Scholar 

  80. Abele, S.; Schmidt, G.; Fleming, M. J.; Steiner, H. Org. Proc. Res. Dev. 2014, 18, 993.

    Article  CAS  Google Scholar 

  81. Chang, M.-Y.; Lee, N.-C.; Lee, M.-F.; Huang, Y.-P.; Lin, C.-H. Tetrahedron Lett. 2010, 51, 5900.

    Article  CAS  Google Scholar 

  82. Lin, X.; Weng, Z. Dalton Trans. 2015, 44, 2021.

    Google Scholar 

  83. Barker, T. J.; Boger, D. L. J. Am. Chem. Soc. 2012, 134, 13588.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  84. Li, Y.; Jiang, X.; Zhao, C.; Fu, X.; Xu, X.; Tang, P. ACS Catal. 2017, 7, 1606.

    Article  CAS  Google Scholar 

  85. Xu, P.; Guo, S.; Wang, L.; Tang, P. Angew. Chem., Int. Ed. 2014, 53, 5955.

    Article  CAS  Google Scholar 

  86. Zhang, X.; Guo, S.; Tang, P. Org. Chem. Front. 2015, 2, 806.

    Article  CAS  Google Scholar 

  87. Li, Z.; Wang, Z.; Zhu, L.; Tan, X.; Li, C. J. Am. Chem. Soc. 2014, 136, 16439.

    Article  CAS  PubMed  Google Scholar 

  88. Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401.

    Article  CAS  PubMed  Google Scholar 

  89. Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2014, 50, 7382.

    Article  CAS  Google Scholar 

  90. Mattson, M. WO Patent WO2011115758 A1.

  91. Yuan, X.; Yao, J.-F.; Tang, Z.-Y. Org. Lett. 2017, 19, 1410.

    Article  CAS  PubMed  Google Scholar 

  92. Vincent, É.; Brioche, J. Eur. J. Org. Chem. 2021, 2421.

  93. Phae-nok, S.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Eur. J. Org. Chem. 2015, 2879.

  94. Roslin, S.; Odell, L. R. Eur. J. Org. Chem. 2017, 1993.

  95. Uygur, M.; Mancheno, O. G. Org. Biomol. Chem. 2019, 17, 5475.

    Article  CAS  PubMed  Google Scholar 

  96. Festa, A. A.; Voskressensky, L. G.; Van der Eycken, E. V. Chem. Soc. Rev. 2019, 48, 4401.

    Article  CAS  PubMed  Google Scholar 

  97. Borodkin, G. I.; Shubin, V. G. Russ. Chem. Rev. 2019, 88, 160.

    Article  CAS  Google Scholar 

  98. Borodkin, G. I.; Elanov, I. R.; Shubin, V. G. Russ. J. Org. Chem. 2021, 57, 301.

    Article  CAS  Google Scholar 

  99. Rueda-Becerril, M.; Mahé, O.; Drouin, M.; Majewski, M. B.; West, J. G.; Wolf, M. O.; Sammis, G. M.; Paquin, J.-F. J. Am. Chem. Soc. 2014, 136, 2637.

    Article  CAS  PubMed  Google Scholar 

  100. Ventre, S.; Petronijevic, F. R.; MacMillan, D.W.C. J. Am. Chem. Soc. 2015, 137, 5654.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  101. Dauncey, E. M.; Morcillo, S. P.; Douglas, J. J.; Sheikh, N. S.; Leonori, D. Angew. Chem., Int. Ed. 2018, 57, 744.

    Article  CAS  Google Scholar 

  102. Lovett, G. H.; Chen, S.; Xue, X.-S.; Houk, K. N.; MacMillan, D. W. C. J. Am. Chem. Soc. 2019, 141, 20031.

    Article  CAS  PubMed  Google Scholar 

  103. Wu, X.; Meng, C.; Yuan, X.; Jia, X.; Qian, X.; Ye, J. Chem. Commun. 2015, 51, 11864.

    Article  CAS  Google Scholar 

  104. Pieber, B.; Shalom, M.; Antonietti, M.; Seeberger, P. H.; Gilmore, K. Angew. Chem., Int. Ed. 2018, 57, 9976.

    Article  CAS  Google Scholar 

  105. Brioche, J. Tetrahedron Lett. 2018, 59, 4387.

    Article  CAS  Google Scholar 

  106. Zhao, J.-J.; Yu, S. Synlett 2021, 391.

  107. Egorov, I. N.; Santra, S.; Kopchuk, D. S.; Kovalev, I. S.; Zyryanov, G. V.; Majee, A.; Ranu, B. C.; Rusinov, V. L.; Chupakhin, O. N. Green Chem. 2020, 22, 302.

    Article  CAS  Google Scholar 

  108. Howard, J. L.; Cao, Q.; Browne, D. L. Chem. Sci. 2018, 9, 3080.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  109. Tan, D.; Friščić, T. Eur. J. Org. Chem. 2018, 18.

  110. Gomollón-Bel, F. Chem. Int. 2019, 41(2), 12.

    Article  Google Scholar 

  111. Zaikin, P. A.; Dyan, O. T.; Elanov, I. R.; Borodkin, G. I. Molecules 2021, 26, 5756.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  112. Howard, J. L.; Nicholson, W.; Sagatov, Y.; Browne, D. L. Beilstein J. Org. Chem. 2017, 13, 1950.

    Google Scholar 

  113. Wang, Y.; Wang, H.; Jiang, Y.; Zhang, C.; Shao, J.; Xu, D. Green Chem. 2017, 19, 1674.

    Article  CAS  Google Scholar 

  114. Kričtofiková, D.; Mečiarová, M.; Rakovský, E.; Šebesta, R. ACS Sustainable Chem. Eng. 2020, 8, 14417.

    Article  Google Scholar 

  115. Hatfield, J. M.; Eidell, C. K.; Stephens, C. E. Tetrahedron Lett. 2013, 54, 1025.

    Article  CAS  Google Scholar 

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Correspondence to Gennady I. Borodkin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(2/3), 84–96

Vyacheslav G. Shubin is deceased

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Borodkin, G.I., Shubin, V.G. Electrophilic Fluorination of Heterocyclic Compounds with NF Reagents in Unconventional Media. Chem Heterocycl Comp 58, 84–96 (2022). https://doi.org/10.1007/s10593-022-03060-3

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