Reaction of 2,3,4,5,6-Pentafluorobenzamide with Potassium Hydride: Unexpected Activation of the C–F Bond and Dimerization of Organofluorine Ligand
- Авторлар: Yambulatov D.S.1, Astaf´eva T.V.1, Voronina J.K.1, Nikolaevskii S.A.1, Kiskin M.A.1, Eremenko I.L.1
- 
							Мекемелер: 
							- Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
 
- Шығарылым: Том 50, № 6 (2024)
- Беттер: 402-410
- Бөлім: Articles
- URL: https://cardiosomatics.ru/0132-344X/article/view/667595
- DOI: https://doi.org/10.31857/S0132344X24060061
- EDN: https://elibrary.ru/MVCLGI
- ID: 667595
Дәйексөз келтіру
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
 
												
	                        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
- Hiyama T. Organofluorine Compounds: Chemistry and Applications. Berlin: Springer, 2000. 272 p.
- Reichenbächer K., Süss H.I., Hulliger J. // Chem. Soc. Rev. 2005. V. 34. P. 22.
- Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Weinheim (Germany): Wiley-VCH, 2013. 320 p.
- Nenajdenko V. Fluorine in Heterocyclic Chemistry. V. 1, 2. Switzerland: Springer International Publishing, 2014. 681 p.
- Amii H., Uneyama K. // Chem. Rev. 2009. V. 109. P. 2119.
- Yang K., Song M., Ali A. I. M. et al. // Chem. Asian J. 2020. V. 15. P. 729.
- Purser S., Moore P.R., Swallow S. // Chem. Soc. Rev. 2008. V. 37. P. 320
- Wang J., Sánchez-Roselló M., Aceña J.L. et al. // Chem. Rev. 2014. V. 114. № 4. P. 2432.
- Nosova E.V., Lipunova G.N., Charushin V.N., Chupakhin O.N. // J. Fluor. Chem. 2018. V. 212. P. 51.
- Mei H., Han J., Klika K.D. et al. // Eur. J. Med. Chem. 2020. V. 186. P. 111826.
- Politanskaya L.V., Selivanova G.A., Panteleeva E.V. et al. // Russ. Chem. Rev. 2019. V. 88. P. 425.
- Ahrens T., Kohlmann J., Ahrens M., Braun T. // Chem. Rev. 2015. V. 115. P. 931.
- Yang S.-D. // Homogeneous Catalysis for Unreactive Bond Activation / Ed. Shi Z.-J., John Wiley & Sons, Inc., 2015. P. 203.
- Unzner T.A., Magauer T. // Tetrahedron Lett. 2015. V. 56. P. 877.
- Politanskaya L., Tretyakov E. // J. Fluor. Chem. 2020. V. 236. P. 109592.
- Fu L., Chen Q., Nishihara Y. // Chem. Rec. 2021. V. 21. P. 3394.
- Ai H.-J., Ma X., Song Q., Wu X.-F. // Sci. China Chem. 2021. V. 64. P. 1630.
- Chen W., Bakewell C., Crimmin M.R. // Synthesis. 2017. V. 49. P. 810.
- Tobisu M., Xu T., Shimasaki T., Chatani N. // J. Am. Chem. Soc. 2011. V. 133. P. 19505.
- Zhang T., Nohira I., Chatani N. // Org. Chem. Front. 2021. V. 8. P. 3783.
- Nohira I., Chatani N. // ACS Catal. 2021. V. 11. P. 4644.
- Kim Y. M., Yu S. // J. Am. Chem. Soc. 2003. V. 125. P. 1696.
- Mikami K., Miyamoto T., Hatano M. // Chem. Commun. 2004. V. 18. P. 2082.
- Cargill M. R., Sandford G., Tadeusiak A. J. et al. // J. Org. Chem. 2010. V. 75. P. 5860.
- Kawamoto K., Kochi T., Sato M. et al. // Tetrahedron Lett. 2011. V. 52. P. 5888.
- Reinhold M.; Grady J.E., Perutz J. // J. Am. Chem. Soc. 2004. V. 126. P. 5268.
- Burling S., Elliott P.I.P., Jasim N. A. et al. // Dalton Trans. 2005. V. 22. P. 3686.
- Nova A., Erhardt S., Jasim N. A. et al. // J. Am. Chem. Soc. 2008. V. 130. P. 15499.
- Chan P.K., Leong W.K. // Organometallics. 2008. V. 27. P. 1247.
- Ishii Y., Chatani N., Yorimitsu S., Murai S. // Chem. Lett. 1998. V. 27. P. 157.
- Vela J., Smith J.M., Yu Y. et al. // J. Am. Chem. Soc. 2005. V. 127. P. 7857.
- Kuehnel M.F., Lentz D., Braun T. // Angew. Chem. Int. Ed. 2013. V. 52. P. 3328.
- Yan G. // Chem. Eur. J. 2022. V. 28. Art. e202200231.
- Li H., Liao S., Xu Y. // Chem. Lett. 1996. V. 25. P. 1059.
- Zhang Y., Liao S., Xu Y. et al. // Synth. Commun. 1997. V. 27. P. 4327.
- Fuchibe K., Akiyama T. // Synlett. 2004. V. 2. P. 1282.
- Robertson D.W., Krushinski J.H., Fuller R.W., Leander J.D.J. // Med. Chem. 1988. V. 31. P. 1418.
- Schultz A.G., Guo Z. // Tetrahedron Lett. 1995. V. 36. P. 659.
- Kowalczyk B.A. // Synthesis. 1997. V. 7. P. 1411.
- Boivin J., Boutillier P., Zard S. Z. // Tetrahedron Lett. 1999. V. 40. P. 2529.
- Rogers J.F., Green D.M. // Tetrahedron Lett. 2002. V. 43. P. 3585.
- Ishihara K., Hasegawa A., Yamamoto H. // Synlett. 2002. P. 1299.
- SMART (Control) and SAINT (Integration) Software. Version 5.0. Madison (WI, USA): Bruker AXS Inc., 1997.
- Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. // J. Appl. Crystallogr. 2015. V. 48. P. 3.
- Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. Appl. Crystallogr. V. 42. 2009. P. 339.
- Sheldrick G.M. // Acta Crystallogr. C. 2015. V. 71. P. 3.
- Prakash G.K.S., Munoz S.B., Papp A. et al. // Asian J. Org. Chem. 2012. V. 1. P. 146.
- Kawazura H., Taketomi T. // J. Polym. Sci. B. 1972. V. 10. P. 265. https://doi.org/10.1002/pol.1972.110100406
- 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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