Department of organofluorine compounds chemistry was founded at 1965 by Professor Lev Yagupolskii. Since 1988 the head of department is Professor Yurii Yagupolskii. There are 3 Doctors of Science, 11 PhDs., 4 engineers and 1 laboratory assistant in this department.

Head of department Prof. Yagupolskii Y.L.
Head of department
Prof. Yagupolskii Y.L.

The priority research field is the elaboration of the methods for fluorinated substituents introduction to the aliphatic, aromatic and heterocyclic compounds. The creation of reagents for nucleophilic and electrophilic perfluoroalkilation is also of interest. The great attention is focused on the study of main groups elements (P, S, Bi, Si) and metals (Cu, Ag, Zn, Fe, Cr, W) fluorine-containing compounds.

The main scientific and practical achievements of the department

The methods for various fluorinated saturated and unsaturated substituents introduction to the aromatic and heterocyclic compounds were developed. The synthetic routs to the aliphatic, aromatic and heterocyclic compounds bearing fluorinated groups with heteroatoms (N, O, S) were found. The organic compounds of phosphorus and iodine with fluorine-containing groups were synthesized.

Electronic nature of various fluorinated groups is also under investigation. Influence of more than 60 fluorine-containing substituents on the aromatic compounds properties has been established and their σ-constants were determined. Professor Lev M. Yagupolskii had formulated a principle of super strong electron-acceptor groups construction by replacement of the sp2-hybridized oxygen atom on the trifluoromethylsulfonylimino group. Using this principle the aza-Curtius, Lossen, Hofmann and Wolff rearrangements were carried out.

The analogs of triflic acid in which oxygen atoms of sulfonyl group are replaced by the trifluoromethylsulfonyl- and nonafluorobuthylsulfonylimino groups were synthesized. It was shown that acidity of these compounds is in excess of triflic acid by 6-9 orders. Bis(trifluoromethylsulfonylimino)trifluoromethanesulfonic acid was found to be an effective catalyst for Friedel-Crafts acylation and cyclization as well as aminolysis of epoxides.

Tris(fluorosulfonyl)methane being the strong CH-acid (рКа = -12.5) was obtained. The last one has the acidity equal to the triflic acid (рКа = -12). This methane derivative was shown to be an effective homogenous catalyst for Friedel-Crafts reaction.

Trifluoromethylated lithium salts which are analogs of lithium hexafluorophosphate were synthesized and investigated. It was found that such compounds are perspective components of chemical current sources due to the high thermal and electrochemical stability.

Thia- and quinocyanine dyes with partly and perfluorinated polymethine chain as well as with fluorine-containing substituents in heterocyclic nuclei have been synthesized and studied. Highly effective sensitizer practically applied in production of color positive film has been created.

New type of ionic liquids bearing polyfluoroalkyl groups at the heterocyclic nitrogen atom was synthesized. It was found that compounds obtained have good temperature characteristics and are stable in neutral and acidic medium.

The new hypotensive medicinal preparation Foridon (calcium channel blocker) containing the difluoromethoxy group has been developed and introduced into clinical practice in collaboration with the Riga Institute of Organic Chemistry, Academy of sciences of Latvia. The new non-steroid antiflogistic product for dermatology and otolaryngology Diftorant containing the SCHF2 group has been put in production at the PJSC SIC «BORSHCHAHIVSKIY CPP». The original drug Flocalin showing cardiotonic activity is currently investigated at the same plant.

Employees of the department

  • prof. Yury Lvovich Yagupolskyi
  • Doctor of Science Kremlev M.M.
  • PhD Pavlenko N.V.
  • PhD, senior researcher Petko K.I.
  • PhD, senior researcher Kirij N.V.
  • PhD, junior researcher Babadzhanova L.A.
  • PhD, senior researcher Sokolenko T.M.
  • PhD, senior researcher Sokolenko L.V.
  • PhD, senior researcher Mushta A.I.
  • PhD, senior researcher Filatov A.A.
  • leading engineer Orlova R.K.
  • 1st category technician Pysarenko M.M.

Articles for 2021-2024

  1. N.V. Pavlenko, Sheng Peng, V. Petrov, A. Jackson, X. Sun, L. Sprague, Yu.L. Yagupolskii Catalytic hydrosilylation of hydrofluoroolefins (HFOs): Synthesis of new fluorinated silanes and diversity of their synthetic character European Journal of Organic Chemistry 33, 5425- 5435 (2020)
  2. L.V. Sokolenko, E.B. Rusanov, Yu.L. Yagupolskii CF3S(O)n-containing olefins in cyclopropanation reactions Journal of Fluorine Chemistry 248, 109802 (2021)
  3. N.V. Kirij, A.A. Filatov, Yu.L. Yagupolskii, Sheng Peng, A. Jackson Synthesis of bis(trifluoromethyl)-alkylated trisubstituted alkenes via highly regeoselective catalyzed hydrosilylation reaction of hexafluoro-2-butyne and their reactivity Journal of Fluorine Chemistry 253, 109922 (2022)
  4. V.V. Rudiuk, A.A. Filatov, L.A. Babadzhanova, Yu.L. Yagupolskii, I.A. Levandovskiy Development of industrial process for the synthesis of the active pharmaceutical ingredient «6-Methyluracil» Voprosy Khimii i Khimicheskoi Tekhnologii 4, 77-82 (2023)
  5. N.V. Kirij, A.A. Filatov, Yu.L. Yagupolskii, Sheng Peng, L. Sprague (E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene Beilstein Journal of Organic Chemistry 20, 452–459 (2024)
  6. L.V. Sokolenko, T.M. Sokolenko, Yu.L. Yagupolskii 1,2-Difluoroethylene (HFO-1132): synthesis and chemistry Beilstein Journal of Organic Chemistry 20, 1955–1966 (2024)
  7. T.M. Sokolenko, Yu.L. Yagupolskii 5-Trifluoromethoxy-substituted Nicotinic Acid, Nicotinamide and Related Compounds Journal of Organic and Pharmaceutical Chemistry 22, 22-30 (2024)