Leninsky Prospect, 47, Moscow
Phone: +7 499 137-29-44
Fax: +7 499 135-53-28

Laboratory for Studies of Homolytic Reactions (N13)

Terent’ev Alexander Olegovich

Dr.Sci, Prof., Corresponding Member of Russian Academy of Sciences (RAS)

e-mail:terentev@ioc.ac.ru, alterex@yandex.ru; phone: +7 916 385 40 80

 

-Deputy Director of N.D. Zelinsky Institute of Organic Chemistry of the RAS

-Head of Laboratory in N. D. Zelinsky Institute of Organic Chemistry of the RAS

-Head of Laboratory in All-Russian Research Institute for Phytopathology, B. Vyazyomy

-Professor in D.I. Mendeleev University of Chemical Technology of Russia, Moscow

 

History of scientific school:

- 1964-2013 - Prof. Gennady Ivanovich Nikishin, Associate Memb. Acad. Sc.;

- 1934-1964 - Prof. Alexander Dmitrievich Petrov, Associate Memb. Acad. Sc.;

- Before this period – Prof. Vladimir Nikolayevich Ipatieff, General-Lieutenant of the Russian army, Member of the Russian Academy of Sciences. Head the research staff of the Universal Oil Products Company in Riverside, Illinois. Lecturer in Chemistry at Northwestern University.

 

Research areas.

  • Chemistry of aliphatic and alicyclic functionalized compounds.
  • Chemistry of peroxides.
  • Reactions with C-, O-, and S-centered radicals.
  • Oxidative coupling reactions.
  • Direct and indirect electroorganic synthesis.
  • Catalysis using transition metals.
  • Homogeneous and heterogeneous catalysis in oxidation reactions.
  • Compounds with antiparasitic, cytotoxic, and antimicrobial activity.
  • Agrochemistry.

 

 

 

 

 

 

 

 

Selected publications of last years:

Lapitskaya, M. A.; Vil’, V. A.; Daeva, E. D.; Terent’ev, A. O.; Pivnitsky, K. K. Alcoholysis of malonyl peroxides to give peracids. Mend. Comm. 2016, 26, 14-15. DOI: 10.1016/j.mencom.2016.01.006

Well-Known Mediators of Selective Oxidation with Unknown Electronic Structure: Metal-Free Generation and EPR Study of Imide-N-Oxyl Radicals.Igor B Krylov, Mykhailo O. Kompanets, Katerina V. Novikova, Iosip O. Opeida, Olga V. Kushch, Boris N. Shelimov, Gennady Ivanovich Nikishin, Dmitri O Levitsky, and Alexander Olegovich Terent'ev. J. Phys. Chem. A, 2016, 120 (1), pp 68–73. DOI: 10.1021/acs.jpca.5b10722

M.D. Vedenyapina, M.Yu. Sharipov, A.O. Terent’ev, A.M. Skundin, A.A. Vedenyapin, [Russian Journal of Physical Chemistry A, 2016, Vol. 90, No. 2, pp. 475–478].

Alexander O. Terent’ev,  Vera A. Vil’, Evgenii S. Gorlov, Gennady I. Nikishin, Kasimir K. Pivnitsky,  Waldemar Adam. Lanthanide-catalyzed oxyfunctionalization of 1,3-diketones, acetoacetic esters, and malonates by oxidative C-O coupling with malonyl peroxides. JOC, 2016, 81, 810-823. DOI: 10.1021/acs.joc.5b02233

Alexander T. Zdvizhkov, Alexander O. Terent’ev, Peter S. Radulov, Roman A. Novikov, Viktor A. Tafeenko, Vladimir V. Chernyshev, Alexey I. Ilovaisky, Dmitri O. Levitsky, Fabrice Fleury, Gennady I. Nikishin, Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I2/H2O2 system, Tetrahedron Letters, 2016, 57, 949–952.  DOI: 10.1016/j.tetlet.2016.01.061

Alexander O. Terent'ev, Zhanna Yu. Pastukhova, Ivan A. Yaremenko, Roman A. Novikov, Dmitry V. Demchuk, Lev G. Bruk, Dmitry O. Levitsky, Fabrice Fleury, Gennady I. Nikishin. Selective transformation of tricyclic peroxides with pronounced antischistosomal activity into 2-hydroxy-1,5-diketones using iron (II) salts. Tetrahedron, 2016, 72, 3421-3426. doi:10.1016/j.tet.2016.04.054

Alexander O. Terent’ev, Mikhail Yu. Sharipov, Alexey P. Glinuskin, Igor B. Krylov, Darya V. Gaidarenko, and Gennady I. Nikishin. Difference in a-thiocyanation of malonates, b-oxo esters and b-diketones with sodium thiocyanate and cerium(iv) ammonium nitrate. Mendeleev Communications, 2016, vol. 26, issue 3, p. 226-227. DOI: 10.1016/j.mencom.2016.05.001

Ashot V. Arzumanyan, Alexander O. Terent’ev, Roman A. Novikov, Valentin G. Lakhtin,  Michail S. Grigoriev, and Gennady I. Nikishin. Reduction of Organosilicon Peroxides: Ring Contraction and Cyclodimerization. Organometallics.  2016, 35, 1667-1673.  DOI: 10.1021/acs.organomet.6b00129

Alexander O. Terent’ev, Zhanna Yu. Pastukhova, Ivan A. Yaremenko, Lev G. Bruk, and Gennady I. Nikishin. Promising hydrogen peroxide stabilizers for large-scale application: unprecedented effect of aryl alkyl ketones. Mendeleev Commun., 2016, 26, 329-331. DOI: 10.1016/j.mencom.2016.07.021

Ivan A. Yaremenko, Vera A. Vil’, Dmitry V. Demchuk and Alexander O. Terent’ev. Rearrangements of organic peroxides and related processes. Beilstein J. Org. Chem. 2016, 12, 1647–1748. doi:10.3762/bjoc.12.162

M.D. Vedenyapina, E.D. Strel’tsova, V.A. Vill’, A.O. Terent’ev, A.A. Vedenyapin. Adsorption of benzoyl peroxide on activated carbon. Solid Fuel Chemistry, 2016, Vol. 50, No. 5, pp. 306–309.

Alexander O. Terent'ev, Olga M. Mulina, Dmitry A. Pirgach, Dmitry V. Demchuk, Mikhail A. Syroeshkin and Gennady I. Nikishin Copper(I)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study. RSC Adv., 2016, 6, 93476-93485. DOI: 10.1039/C6RA19190H

Alexander O. Terent’ev, Olga M. Mulina, Dmitry A. Pirgach, Mikhail A. Syroeshkin, Alexey P. Glinushkin and Gennady I. Nikishin. Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines. Mendeleev Commun., 2016, 26, 538–539. DOI: 10.1016/j.mencom.2016.11.027

Ivan A. Yaremenko, Mikhail A. Syroeshkin, Dmitri O. Levitsky, Fabrice Fleury, Alexander O. Terent’ev. Cyclic peroxides as promising anticancer agents: in vitro cytotoxicity study of synthetic ozonides and tetraoxanes on human prostate cancer cell lines. Medicinal Chemistry Research, 2017, Volume 26, Issue 1, pp 170–179, DOI 10.1007/s00044-016-1736-2

Vera A. Vil’, Ivan A. Yaremenko, Alexey I. Ilovaisky and Alexander O. Terent’ev, Synthetic Strategies for Peroxide Ring Construction in Artemisinin, Molecules. 2017, 22(1), 117; doi: 10.3390/molecules22010117

 Gennady I. Nikishin, Nadezhda I. Kapustina, Lyubov' L. Sokova, Oleg V. Bityukov, Alexander O. Terent'ev. One-pot oxidative bromination – Esterification of aldehydes to 2-bromoesters using cerium (IV) ammonium nitrate and lithium bromide. Tetrahedron Letters, 2017, 58 (4), 352–354. DOI: 10.1016/j.tetlet.2016.12.036

dos Passos Gomes, G., Yaremenko, I. A., Radulov, P. S., Novikov, R. A., Chernyshev, V. V., Korlyukov, A. A., Nikishin, G. I., Alabugin, I. V. and Terent'ev, A. O. (2017), Stereoelectronic Control in the Ozone-Free Synthesis of Ozonides. Angew. Chem. Int. Ed. 2017, 56, 4955-4959. doi: 10.1002/anie.201610699

Alexander O. Terent’ev, Vera A. Vil’, Evgenii S. Gorlov, Olga N. Rusina, Alexander A. Korlyukov, Gennady I. Nikishin, and Waldemar Adam. Selective Oxidative Coupling of 3H-Pyrazol-3-ones, Isoxazol-5(2H)-ones, Pyrazolidine-3,5-diones, and Barbituric Acids with Malonyl Peroxides: An Effective C-O Functionalization. Chemistry Select. 2017, 2, 3334-3341. DOI: 10.1002/slct.201700720

Margarita A. Lapitskaya, Vera A. Vil’, Ludmila L. Vasil’eva, Elena D. Daeva, Alexander O. Terent’ev and Kasimir K. Pivnitsky. Spontaneous reaction of malonyl peroxides with methanol. Mendeleev Commun., 2017, vol. 27, issue 3, p. 243-245. DOI: 10.1016/j.mencom.2017.05.008

Oleg V. Bityukov,Vera A. Vil’,Valentina M. Merkulova, Gennady I. Nikishin andAlexander O. Terent’ev. Silica gel mediated oxidative C-O coupling of β-dicarbonyl compounds with malonyl peroxides in solvent-free conditions. Pure and Applied Chemistry 2017 in press.

Mikhail A. Syroeshkin, Igor B. Krylov, Audrey M. Hughes, Igor V. Alabugin, Darya V. Nasybullina, Mikhail Yu. Sharipov, Vadim P. Gultyai, Alexander O. Terent’ev. Electrochemical behavior of N-oxyphthalimides: Cascades initiating self-sustaining catalytic reductive N-O bond cleavage J Phys Org Chem. 2017, 30 (9), 3744DOI: 10.1002/poc.3744

Igor B. Krylov,  Stanislav A. Paveliev,  Boris N. Shelimov,  Boris V. Lokshin,  Irina A. Garbuzova,  Viktor A. Tafeenko,  Vladimir V. Chernyshev,  Alexander S. Budnikov,  Gennady I. Nikishin  and  Alexander O. Terent'ev. Selective cross-dehydrogenative C-O coupling of N-hydroxy compounds with pyrazolones. Introduction of diacetyliminoxyl radical into practice of organic synthesis. Org. Chem. Front., 2017, 4, 1947-1957. DOI: 10.1039/C7QO00447H

 A. O. Terent'ev, O. M. Mulina, D. A. Pirgach, A. I. Ilovaisky , M. A. Syroeshkin, N. I. Kapustina, G. I. Nikishin Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: an electrochemical mechanistic study Tetrahedron, 2017, 73, 6871-6879.

Novel Peroxides as Promising Anticancer Agents with Unexpected Depressed Antimalarial Activity. Coghi, Paolo, Yaremenko, Ivan A., Prommana, Parichat, Radulov, Peter S., Syroeshkin, Mikhail A., Wu, Yu Jun, Gao, Jia Ying, Gordillo, Floria M., Mok, Simon, Wong, Vincent Kam Wai, Uthaipibull, Chairat, Terent'ev, Alexander O. CHEMMEDCHEM. 2018, 13(9), 902-908   DOI: 10.1002/cmdc.201700804

Ozone-Free Synthesis of Ozonides: Assembling Bicyclic Structures from 1,5-Diketones and Hydrogen Peroxide. Yaremenko, Ivan A.,  Gomes, Gabriel dos Passos, Radulov, Peter S., Belyakova, Yulia Yu., Vilikotskiy, Anatoliy E., Vil', Vera A., Korlyukov, Alexander A., Nikishin, Gennady I., Alabugin, Igor V., Terent'ev, Alexander O. The Journal of Organic Chemistry. 2018, 83(8), 4402-4426. DOI: 10.1021/acs.joc.8b00130

Vera A. Vil', Gabriel dos Passos Gomes, Oleg V. Bityukov, Konstantin A. Lyssenko, Gennady I. Nikishin, Igor V. Alabugin, Alexander O. Terent’ev, Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate. Angew. Chem. Int. Ed. 2018, 130 (13), 3430-3434. doi:10.1002/anie.201712651.

Vera A. Vil’, Tatyana A. Gloriozova, Vladimir V. Poroikov, Alexander O. Terent’ev, Nick Savidov, Valery M. Dembitsky. Peroxy steroids derived from plant and fungi and their biological activities. Applied Microbiology and Biotechnology, 2018, 102 (18), 7657–7667. DOI:10.1007/s00253-018-9211-2

Margarita A. Lapitskaya, Vera A. Vil’, Elena D. Daeva, Alexander O. Terent’ev, Kasimir K. Pivnitsky, Dimethylmalonoyl peroxide – the neglected lowest homologue: simple synthesis and high reactivity. Mendeleev Commun., 2018, 28 (5), 505-507. doi:10.1016/j.mencom.2018.09.018.

Vera A. Vil’, Gabriel dos Passos Gomes, Maria V. Ekimova, Konstantin A. Lyssenko, Mikhail A. Syroeshkin, Gennady I. Nikishin, Igor V. Alabugin, Alexander O. Terent’ev, Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones. J. Org. Chem., 2018, 83 (21), 13427–13445. DOI: 10.1021/acs.joc.8b02218.

 Igor B. Krylov, Stanislav A. Paveliev, Natalia S. Shumakova, Mikhail A. Syroeshkin, Boris N. Shelimov, Gennady I. Nikishin and Alexander O. Terent’ev. Iminoxyl radicals vs. tert-butylperoxyl radical in competitive oxidative C-O coupling with β-dicarbonyl compounds. Oxime ether formation prevails over Kharasch peroxidation. RSC Adv.2018, 8, 5670-5677. DOI: 10.1039/C7RA13587D

 Igor B. Krylov, Stanislav A. Paveliev, Mikhail A. Syroeshkin, Alexander A. Korlyukov, Pavel V. Dorovatovskii, Yan V. Zubavichus, Gennady I. Nikishin and Alexander O. Terent’ev. Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes. Beilstein J. Org. Chem. 2018, 14, 2146-2155. DOI:10.3762/bjoc.14.188

 O. M. Mulina, A. I. Ilovaisky, A. O. Terent’ev Oxidative coupling with S-N bond formation Eur. J. Org. Chem., 2018, 4648-4672.

A. O. Terent’ev, O. M. Mulina, A. I. Ilovaisky, V. A. Kokorekin, G. I. Nikishin Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols Mendeleev Commun., 2019, 29, 80-82.

A. O. Terent’ev, O. M. Mulina, V. D. Parshin, V. A. Kokorekin, G. I. Nikishin Electrochemically induced oxidative S–O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles Org. Biomol. Chem., 2019 DOI: 10.1039/c8ob03162b.

Oleg V. Bityukov, Olesya K. Matveeva, Vera A. Vil’, Vladimir A. Kokorekin, Gennady I. Nikishin, Alexander O. Terent’ev, Electrochemically Induced Intermolecular Cross-Dehydrogenative C–O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids. J. Org. Chem., 2019, 84 (3), pp 1448–1460. DOI10.1021/acs.joc.8b02791.

Oleg V. Bityukov, Vera A. Vil’, Nikita V. Lukashin, Aleksandr G. Cherednichenko, Gennady I. Nikishin, Alexander O. Terent’ev, Solvent-free silica gel mediated decarboxylation of C–O coupling products of β-diketones and β-oxo esters with malonyl peroxides. Mendeleev Commun., 2019, 29 (1), 55-56. doi:10.1016/j.mencom.2019.01.017.

Vera Vil’, Alexander O. Terent’ev, Abed Al Aziz Al Quntar, Tatyana A. Gloriozova, Nick Savidov, Valery M. Dembitsky, Oxetane-containing metabolites: origin, structures, and biological activities. Appl. Microbiol. Biotechnol., 2019, 1-19. doi:10.1007/s00253-018-09576-z.

Vera A. Vil’, Tatyana A. Gloriozova, Alexander O. Terent’ev, Nick Savidov, Valery M. Dembitsky, Hydroperoxides derived from marine sources: origin and biological activities. Appl. Microbiol. Biotechnol., 2019, 103, 1627-1642. doi:10.1007/s00253-018-9560-x.

 

Conferences organized by Institute:

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Important events:

Congratulations! Valentine Ananikov has been elected to Academia Europaea! The European Academy of Sciences (Academia Europaea) was founded in 1988. It unites about four thousand globally acknowledged experts in mathematics, medicine, natural sciences, humanities, law, economy, and social and political sciences from many countries of Europe. Among its members are also European scientists who live in other regions of the world. Currently, it includes seventy two Nobel laureates and it should be highlighted that many of them were elected to the Academy before winning the Prize.
Professor Mario Pargliaro Lecturing at Zelinsky Institute Prof Mario Pagliaro (Palermo Italy) gave two talks on June 8th and 9th.
Selective In-Situ Metal Azide Reactions Alexey Sukhorukov, N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia, and colleagues studied the selective reactions of in-situ generated metal azides on N,N-bis(oxy)enamines. By combining readily generated bis(oxy)enamine substrates with sodium azide and one of a variety of metal salts (including Mg, Cu, Zn, Co, and Ni), the researchers showed that the metal cation selectively alters the mechanism to favor the formation of specific organoazide products.
On February 1st, Prof. Gleb Sukhorukov from the School of Engineering and Materials Science, Queen Mary, University of London, gave a lecture “Remote Controlled Delivery Nanosystems” at ZIOC.
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