The Laboratory was established in 2015 on the basis of the Institute of Organic Chemistry of the National Academy of Sciences of Ukraine (NASU) from employees of the L.M. Litvinenko Institute of Physical Organic and Coal Chemistry (InPOCC) of NASU. Head of the Laboratory is D.Sci, Prof. M.I. Korotkikh, who previously headed the InPOCC department. The Laboratory employs 1 doctor, 4 PhD and 1 engineer.
The main scientific direction of the Laboratory is related to the study of chemistry of stable carbenes, in particular, the synthesis of stable carbenes, their derivatives, including carbene complexes of transition metals, the study of reactions involving carbene and carbenoid transformations. Particular attention is paid to the study of the catalytic efficiency of carbenes and carbene complexes in organic reactions and the biological activity of carbenoid compounds.
The main scientific and practical achievements of the Laboratory
In the field of synthesis of stable carbenes and their derivatives
Effective methods for the synthesis of stable carbenes of the series of imidazole, benzimidazole and 1,2,4-triazole have been developed. The first representative of benzimidazole series carbenes was synthesized - 1,3-di (1-adamantyl) benzimi¬dazol-2-ylidene, 1-alkyl-3,4-diaryl-substituted 1,2,4-triazol-5-ylidenes, including compounds with several fluorine and chlorine atoms, among which the lowest basic compounds among all stable carbenes were found, new sterically shielded 1,3,4-triaryl-1,2,4-triazol-5-ylidenes, 1,3-diarylimidazol-2- ylidenes. New methods for the preparation of carbenes have been developed: 1) via their cyanomethyl derivatives of azolines – the products of carbene insertion into the C-H bond of acetonitrile, and 2) by direct deprotonation of 1,2,4-triazolium salts in acetonitrile. A series of carbene complexes of copper (I), silver, nickel, palladium, rhodium, iron and manganese was obtained. New methods for the synthesis of carbene complexes have been developed on the basis of carbenoid compounds - 2-cyanomethyl derivatives of 2H-imidazolines and 2H-benzimidazolines and metal salts, as well as from mesoionic compounds and metal salts, in situ versions of the synthesis of carbene complexes of copper(I), silver, palladium and rhodium, which exhibit catalytic and biological activity.
In the field of studying new carbene reactions
A new reaction of carbenes with malonic ester was discovered, which leads to heterocyclic zwitterionic compounds. An induced tandem autotransformation of 1,2,4-triazol-5-ylidenes into 5-amidino-1,2,4-triazole derivatives was found. The new reaction of cleavage of 1,3-di(1-adamantylamino) carbenes in aliphatic nitryles into N-cyanovinyl-N-adamantylamines has been revealed. The reaction of stable carbenes with cyclic esters (propanesultone) and activated olefins to form zwitterionic compounds has been developed.
In the field of study of catalytic efficiency of carbenes and their derivatives
A high catalytic effect of heterocyclic carbenes has been established in the transesterification reaction, which allows not only to use catalysis in organic synthesis, but also to obtain biodiesel fuel from oils in a technologically convenient process. The highest catalytic effect of carbenes in the benzoin condensation reaction was found.
The highest catalytic effect of sterically shielded complexes of imidazol-2-ylidenes with palladium halides in the reaction of hydrodegalogenation of haloarenes was revealed, which allows to propose a new technology of decontamination of persistent organic pollutants by the action of metal alkoxides. The solution of this problem is of global importance. The highest catalytic effect of carbene complexes in the reaction of hydrogen transfer reduction of multiple bonds (ketones, imines) in an alkaline alcohol medium, which can be used in organic synthesis, has been found. A high catalytic effect of copper (I) carbene complexes in the Huisgen reaction (cycloaddition of azides to acetylenes) has been established. A high catalytic effect of sterically shielded palladium carbene complexes was found, including PEPPSI-catalysts, in C-C-coupling (Suzuki-Miyaura and Sonogashira) and C-N-coupling (Buchwald-Hartwig) reactions, which is important for solving problems of organic synthesis. A high catalytic effect of rhodium carbene complexes in the reduction reactions of fluoroarenes with hydrogen with preservation of fluorine atoms was revealed, which allows obtaining steroselectively fluoro-substituted cycloaliphatic compounds. Together with the Institute of Physical Organic and Coal Chemistry of the National Academy of Sciences, a high catalytic effect of the copper(I) ionic carbene complex in the oxidation of cumene with oxygen in the presence of N-hydroxyphthalimide was found.
In the field of studying the biological activity of carbenoid derivatives
High antimicrobial activity (on strains of bacteria and fungi) of a number of carbene complexes of copper(I), silver, rhodium and organic salts containing adamantyl, long-chain aliphatic and macrocyclic fragments has been revealed, which can be used in the search for new drugs of this action. New carbene and other organic complexes have been found that have antimicrobial activity equal to or higher than that for known antiseptic (1-cetylpyridinium chloride) and antifungal (clotrimazole, bifonazole) drugs.
Departmental projects (state funding):
«Stable carbenes of the heterocyclic and acyclic series. Catalytic properties in nucleophilic halogen substitution reactions of haloarenes».
«Development of technological solutions for the needs of defense and military medicine: functionalized compounds, solid rocket fuels, catalytic systems for neutralization of chemical weapons components, flame retardant coatings, biologically active substances. Part. 2. Development of methods for obtaining rocket fuel components. Development of methods of catalytic regenerative decontamination of combat poisons. Study of antimicrobial activity of carbene complexes».
Employees of the department:
- Head of Laboratory, D. Sci., Professor Korotkikh Mykola Ivanovich
- D. Ph., Senior Researcher Sabierov Vagiz Shamiliovich
- D. Ph., Researcher Yenya Vasil Ivanovich
- D. Ph., Senior Researcher Shumeiko Olexander Yevgenovich
- D. Ph., Senior Researcher Vakhitova Liubov Mykolaivna
- Engineer Avksentiev Olexander Sergiyevich
Scientific and scientific-technical cooperation:
- RPE «Ukrorgsynthez Ltd», RPE «Enamine Ltd» (м. Київ).
- L.M. Litvinenko Institute of Physical Organic and Coal Chemistry of NASU
- Donetsk National University (Vinnitsya)
- National University «Lviv Polytechnika»
The most important articles published in 2020-2024:
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N. I. Korotkikh, V. Sh. Saberov, G. F. Rayenko, V. I. Yenya, O. S. Avksentiev, N. V. Glinyanaya, O. P. Shvaika Carbene complexes of palladium are effective catalysts of haloarene hydrodehalogenation reaction. In monograph «New functional substances and materials of chemical production» Academperiodica. 2021. С. 255-267
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N. V. Glinyanaya, Rayenko G. F., Korotkikh N. I., Rusanov E. B., Ryabitsky A. B., Okolovska L. G., Shvaika O. P. Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations RSC Advances. 2021. Vol. 11. Р. 30841-30848
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V. Sh. Saberov, O. S. Avksentiev, G. F. Rayenko, A. B. Ryabitsky, V. I. Yenya, M. M. Nechitaylov, N. I. Korotkikh Catalysis of the hydrodehalogenation reaction of haloarenes by palladium carbene PEPPSI complexes Ukr. Chem. J. 2022. Vol. 88 (1). Р. 67–81
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G. F. Rayenko, O. S. Avksentiev, V. Sh. Saberov, A. B. Ryabitsky, V. I. Yenya, O. Z. Komarovska-Porokhnyavets, V. I. Lubenets, N. I. Korotkikh Synthesis and the Antimicrobial Activity of Salt Carbenoid Compounds J. Org. Pharm. Chem. 2022. Vol. 20 (2). P. 14–26
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G. F. Rayenko, A. S. Avksentiev, V. Sh. Saberov, E. B. Rusanov, A. B. Ryabitsky, S. V. Shishkina, O. Z. Komarovska-Porokhnyavets, V. I. Lubenets, N. I. Korotkikh Synthesis and Antimicrobial Activity of Carbene Complexes of the Imidazole, Benzimidazole and 1,2,4-Triazole Series ChemistrySelect. 2023. Vol. 8. e202203143
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V. Sh. Saberov, G. F. Rayenko, A. S. Avksentiev, L. M. Vakhitova, N. I. Korotkikh Catalytic hydrodehalogenation of haloarenes with hydrogen and hydrogen-containing compounds Theor. Exper. Chem. 2023. Vol. 59. № 3. Р. 151-177
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A. S. Avksentiev, V. Sh. Saberov, G. F. Rayenko, A. B. Ryabitsky, E. V. Polunkin, S. M. Pleskun, N.I. Korotkikh Catalysis of the Transesterification Reaction of Alkyl Benzoates and Vegetable Oils by Carbonates, Carbene, and Anionite Theor. Exper. Chem. 2024. Vol. 59. № 3. Р. 427-433
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V. Sh. Sabierov, N.I. Korotkikh, A. S. Avksentiev, V. I. Yenya, G. F. Rayenko Catalytic Properties of Sterically Shielded Carbene Complexes of Palladium in C–C and C–N Coupling Reactions of Haloarenes Theor. Exper. Chem. 2024. Vol. 59. № 3. Р. 418-426
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N. I. Korotkikh, G. F. Rayenko, V. Sh. Saberov, V.I. Yenya, L.M. Vakhitova, A. V. Kiselyov Philicity indices of carbenes Comp. Theor. Chem. 2024. Vol. 1238. 114728
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V. Sh. Saberov, G. F. Rayenko, A. S. Avksentiev, L. M. Vakhitova, N. I. Korotkikh Catalytic hydrodehalogenation of haloarenes: electron transfer reactions and related transformations Theor. Exper. Chem. 2024. Т. 60. № 1. P. 3–30
Study guides:
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Ol. Shvayka, M. Korotkih The beginnings of the chemistry of heterocyclic compounds Study guide. Kyiv: Akademperiodika. – 2020. – 194 p., 12.29 printed sheets
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Ol. Shvayka, M. Korotkih, G. Rayenko Fundamentals of the synthesis of organic substances Study guide. Kyiv: Akademperiodika. – 2021. – 337 p., 21.09 printed sheets
The most important articles published in 2020-2024
The most important articles published in 2020-2024
-
N. I. Korotkikh, V. Sh. Saberov, G. F. Rayenko, V. I. Yenya, O. S. Avksentiev, N. V. Glinyanaya, O. P. Shvaika Carbene complexes of palladium are effective catalysts of haloarene hydrodehalogenation reaction. In monograph «New functional substances and materials of chemical production» Academperiodica. 2021. С. 255-267
-
N. V. Glinyanaya, Rayenko G. F., Korotkikh N. I., Rusanov E. B., Ryabitsky A. B., Okolovska L. G., Shvaika O. P. Halogen-containing heteroaromatic carbenes of the 1,2,4-triazole series and their transformations RSC Advances. 2021. Vol. 11. Р. 30841-30848
-
V. Sh. Saberov, O. S. Avksentiev, G. F. Rayenko, A. B. Ryabitsky, V. I. Yenya, M. M. Nechitaylov, N. I. Korotkikh Catalysis of the hydrodehalogenation reaction of haloarenes by palladium carbene PEPPSI complexes Ukr. Chem. J. 2022. Vol. 88 (1). Р. 67–81
-
G. F. Rayenko, O. S. Avksentiev, V. Sh. Saberov, A. B. Ryabitsky, V. I. Yenya, O. Z. Komarovska-Porokhnyavets, V. I. Lubenets, N. I. Korotkikh Synthesis and the Antimicrobial Activity of Salt Carbenoid Compounds J. Org. Pharm. Chem. 2022. Vol. 20 (2). P. 14–26
-
G. F. Rayenko, A. S. Avksentiev, V. Sh. Saberov, E. B. Rusanov, A. B. Ryabitsky, S. V. Shishkina, O. Z. Komarovska-Porokhnyavets, V. I. Lubenets, N. I. Korotkikh Synthesis and Antimicrobial Activity of Carbene Complexes of the Imidazole, Benzimidazole and 1,2,4-Triazole Series ChemistrySelect. 2023. Vol. 8. e202203143
-
V. Sh. Saberov, G. F. Rayenko, A. S. Avksentiev, L. M. Vakhitova, N. I. Korotkikh Catalytic hydrodehalogenation of haloarenes with hydrogen and hydrogen-containing compounds Theor. Exper. Chem. 2023. Vol. 59. № 3. Р. 151-177
-
A. S. Avksentiev, V. Sh. Saberov, G. F. Rayenko, A. B. Ryabitsky, E. V. Polunkin, S. M. Pleskun, N.I. Korotkikh Catalysis of the Transesterification Reaction of Alkyl Benzoates and Vegetable Oils by Carbonates, Carbene, and Anionite Theor. Exper. Chem. 2024. Vol. 59. № 3. Р. 427-433
-
V. Sh. Sabierov, N.I. Korotkikh, A. S. Avksentiev, V. I. Yenya, G. F. Rayenko Catalytic Properties of Sterically Shielded Carbene Complexes of Palladium in C–C and C–N Coupling Reactions of Haloarenes Theor. Exper. Chem. 2024. Vol. 59. № 3. Р. 418-426
-
N. I. Korotkikh, G. F. Rayenko, V. Sh. Saberov, V.I. Yenya, L.M. Vakhitova, A. V. Kiselyov Philicity indices of carbenes Comp. Theor. Chem. 2024. Vol. 1238. 114728
-
V. Sh. Saberov, G. F. Rayenko, A. S. Avksentiev, L. M. Vakhitova, N. I. Korotkikh Catalytic hydrodehalogenation of haloarenes: electron transfer reactions and related transformations Theor. Exper. Chem. 2024. Т. 60. № 1. P. 3–30
Study guides
Study guides
-
Ol. Shvayka, M. Korotkih The beginnings of the chemistry of heterocyclic compounds Study guide. Kyiv: Akademperiodika. – 2020. – 194 p., 12.29 printed sheets
-
Ol. Shvayka, M. Korotkih, G. Rayenko Fundamentals of the synthesis of organic substances Study guide. Kyiv: Akademperiodika. – 2021. – 337 p., 21.09 printed sheets
The Major Scientific and Practical Achievements of the Department
The Major Scientific and Practical Achievements of the Department












