Russian Journal of General Chemistry. Vol. 92, No. 9, Pages 1712-1719, 2022

P. A. Volkov^a, K. O. Khrapova^a, A. A. Telezhkin^a, A. I. Albanov^a, K. A. Apartsin^b, and B. A. Trofimov^a^,*

^aA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033 Russia

^bIrkutsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033 Russia

Abstract— The S_N^HAr reaction of pyridines with bis(polyfluoroalkyl)phosphonates assisted by benzoylphenylacetylene (equimolar reactants ratio, 70–75°С, 3.5–7 h, catalyst- and solvent-free) has led to bis(polyfluoroalkyl)pyridinylphosphonates in yield up to 51%. In the presence of phenylcyanoacetylene, pyridine has reacted with bis(2,2,2-trifluoroethyl)phosphonate at room temperature to regio- and stereoselectively form Z-(cyanophenylethenyl)-1,4-dihydropyridin-4-ylphosphonate, the S_N^HAr reaction kinetic product, in high yield.

Keywords: pyridines, acetylenes, bis(polyfluoroalkyl)phosphonates, zwitterions, S_N^HAr reaction

SNHAr Reaction of Pyridines with Bis(polyfluoroalkyl)phosphonates Assisted by Electron-Deficient Acetylenes

S_N^HAr Reaction of Pyridines with Bis(polyfluoroalkyl)phosphonates Assisted by Electron-Deficient Acetylenes