Reaction of 2,3,4,5,6-Pentafluorobenzamide with Potassium Hydride: Unexpected Activation of the C–F Bond and Dimerization of Organofluorine Ligand

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The reaction of potassium hydride with 2,3,4,5,6-pentafluorobenzamide (FBAm) in dimethoxyethane results in activation of the C–F bond in the para-position to the C(O)NH2 group followed by dimerization of FBAm to form a potassium salt with one free amide group. The structure of the binuclear reaction product {(DME)2K+[C6F5–C(O)N–C6F4–C(O)NH2]–}2 (I) was determined by X-ray diffraction (CCDC 2311402), the purity of the product was confirmed by NMR spectroscopy.

Толық мәтін

Рұқсат жабық

Авторлар туралы

D. Yambulatov

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: yambulatov@yandex.ru
Ресей, Moscow

T. Astaf´eva

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Ресей, Moscow

J. Voronina

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Ресей, Moscow

S. Nikolaevskii

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: sanikol@igic.ras.ru
Ресей, Moscow

M. Kiskin

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Ресей, Moscow

I. Eremenko

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: yambulatov@yandex.ru
Ресей, Moscow

Әдебиет тізімі

  1. Hiyama T. Organofluorine Compounds: Chemistry and Applications. Berlin: Springer, 2000. 272 p.
  2. Reichenbächer K., Süss H.I., Hulliger J. // Chem. Soc. Rev. 2005. V. 34. P. 22.
  3. Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Weinheim (Germany): Wiley-VCH, 2013. 320 p.
  4. Nenajdenko V. Fluorine in Heterocyclic Chemistry. V. 1, 2. Switzerland: Springer International Publishing, 2014. 681 p.
  5. Amii H., Uneyama K. // Chem. Rev. 2009. V. 109. P. 2119.
  6. Yang K., Song M., Ali A. I. M. et al. // Chem. Asian J. 2020. V. 15. P. 729.
  7. Purser S., Moore P.R., Swallow S. // Chem. Soc. Rev. 2008. V. 37. P. 320
  8. Wang J., Sánchez-Roselló M., Aceña J.L. et al. // Chem. Rev. 2014. V. 114. № 4. P. 2432.
  9. Nosova E.V., Lipunova G.N., Charushin V.N., Chupakhin O.N. // J. Fluor. Chem. 2018. V. 212. P. 51.
  10. Mei H., Han J., Klika K.D. et al. // Eur. J. Med. Chem. 2020. V. 186. P. 111826.
  11. Politanskaya L.V., Selivanova G.A., Panteleeva E.V. et al. // Russ. Chem. Rev. 2019. V. 88. P. 425.
  12. Ahrens T., Kohlmann J., Ahrens M., Braun T. // Chem. Rev. 2015. V. 115. P. 931.
  13. Yang S.-D. // Homogeneous Catalysis for Unreactive Bond Activation / Ed. Shi Z.-J., John Wiley & Sons, Inc., 2015. P. 203.
  14. Unzner T.A., Magauer T. // Tetrahedron Lett. 2015. V. 56. P. 877.
  15. Politanskaya L., Tretyakov E. // J. Fluor. Chem. 2020. V. 236. P. 109592.
  16. Fu L., Chen Q., Nishihara Y. // Chem. Rec. 2021. V. 21. P. 3394.
  17. Ai H.-J., Ma X., Song Q., Wu X.-F. // Sci. China Chem. 2021. V. 64. P. 1630.
  18. Chen W., Bakewell C., Crimmin M.R. // Synthesis. 2017. V. 49. P. 810.
  19. Tobisu M., Xu T., Shimasaki T., Chatani N. // J. Am. Chem. Soc. 2011. V. 133. P. 19505.
  20. Zhang T., Nohira I., Chatani N. // Org. Chem. Front. 2021. V. 8. P. 3783.
  21. Nohira I., Chatani N. // ACS Catal. 2021. V. 11. P. 4644.
  22. Kim Y. M., Yu S. // J. Am. Chem. Soc. 2003. V. 125. P. 1696.
  23. Mikami K., Miyamoto T., Hatano M. // Chem. Commun. 2004. V. 18. P. 2082.
  24. Cargill M. R., Sandford G., Tadeusiak A. J. et al. // J. Org. Chem. 2010. V. 75. P. 5860.
  25. Kawamoto K., Kochi T., Sato M. et al. // Tetrahedron Lett. 2011. V. 52. P. 5888.
  26. Reinhold M.; Grady J.E., Perutz J. // J. Am. Chem. Soc. 2004. V. 126. P. 5268.
  27. Burling S., Elliott P.I.P., Jasim N. A. et al. // Dalton Trans. 2005. V. 22. P. 3686.
  28. Nova A., Erhardt S., Jasim N. A. et al. // J. Am. Chem. Soc. 2008. V. 130. P. 15499.
  29. Chan P.K., Leong W.K. // Organometallics. 2008. V. 27. P. 1247.
  30. Ishii Y., Chatani N., Yorimitsu S., Murai S. // Chem. Lett. 1998. V. 27. P. 157.
  31. Vela J., Smith J.M., Yu Y. et al. // J. Am. Chem. Soc. 2005. V. 127. P. 7857.
  32. Kuehnel M.F., Lentz D., Braun T. // Angew. Chem. Int. Ed. 2013. V. 52. P. 3328.
  33. Yan G. // Chem. Eur. J. 2022. V. 28. Art. e202200231.
  34. Li H., Liao S., Xu Y. // Chem. Lett. 1996. V. 25. P. 1059.
  35. Zhang Y., Liao S., Xu Y. et al. // Synth. Commun. 1997. V. 27. P. 4327.
  36. Fuchibe K., Akiyama T. // Synlett. 2004. V. 2. P. 1282.
  37. Robertson D.W., Krushinski J.H., Fuller R.W., Leander J.D.J. // Med. Chem. 1988. V. 31. P. 1418.
  38. Schultz A.G., Guo Z. // Tetrahedron Lett. 1995. V. 36. P. 659.
  39. Kowalczyk B.A. // Synthesis. 1997. V. 7. P. 1411.
  40. Boivin J., Boutillier P., Zard S. Z. // Tetrahedron Lett. 1999. V. 40. P. 2529.
  41. Rogers J.F., Green D.M. // Tetrahedron Lett. 2002. V. 43. P. 3585.
  42. Ishihara K., Hasegawa A., Yamamoto H. // Synlett. 2002. P. 1299.
  43. SMART (Control) and SAINT (Integration) Software. Version 5.0. Madison (WI, USA): Bruker AXS Inc., 1997.
  44. Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. // J. Appl. Crystallogr. 2015. V. 48. P. 3.
  45. Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. Appl. Crystallogr. V. 42. 2009. P. 339.
  46. Sheldrick G.M. // Acta Crystallogr. C. 2015. V. 71. P. 3.
  47. Prakash G.K.S., Munoz S.B., Papp A. et al. // Asian J. Org. Chem. 2012. V. 1. P. 146.
  48. Kawazura H., Taketomi T. // J. Polym. Sci. B. 1972. V. 10. P. 265. https://doi.org/10.1002/pol.1972.110100406
  49. Sergeev V.A., Shitikov V.K., Nedel´kin V.I. // Russ. Chem. Rev. 1978. V. 47. P. 1095. https://doi.org/10.1070/RC1978v047n11ABEH002295

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2. Fig. 1. Molecular structures of two independent molecules A (a) and B (b) in complex I (thermal ellipsoids with a probability of 30%, solvate molecules and disordering of DME molecules in molecule A are not shown).

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3. Fig. 2. Fragment of packing I in a crystal (hydrogen atoms in DME molecules and solvate molecules are not shown; dotted lines indicate H-bonds and interactions C=O...π, π...π).

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4. Scheme 1.

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5. Scheme 2.

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