Dr. Vsevolod A. Peshkov
Dr. Vsevolod A. Peshkov received his Diploma in Chemistry in 2008 from Lomonosov Moscow State University with Prof. Nikolay V. Lukashev. In 2009, he joined the group of Prof. Erik V. Van der Eycken at the University of Leuven (KU Leuven) as a doctoral student. He defended his doctoral thesis entitled “Synthesis of nitrogen-containing medium-sized rings fused with benzene or indole through transition metal-catalyzed carbocyclizations” in 2013. He then spent one year at the University of Pittsburgh working on several medicinal chemistry projects under Prof. Peter Wipf and Prof. Donna Huryn’s direction. In September 2014, he began his independent career at Soochow University, China. In August 2018, he took on the position of Assistant Professor and Chemistry Graduate Program Director at Nazarbayev University, Kazakhstan. His research centers on a diversity-oriented synthesis (DOS) of complex heterocyclic molecules using multicomponent, one-pot and tandem strategies. In addition, his research group is active in design and synthesis of novel fluorescent organic materials and their optical properties assessment.
Research Program
The first research direction pursued by my group deals with the application of multicomponent reactions (MCRs) and subsequent post-MCR transformations for the assembly of biologically relevant heterocyclic scaffolds. For example, we have been extensively utilizing a Ugi four-component reaction (U4CR) of amine, aldehyde, carboxylic acid and isocyanide towards the subsequent upgrade of resulting acyclic Ugi adducts into a large variety of heterocycles. Thanks to remarkable robustness of Ugi reaction and its broad functional group tolerance we were able to thoroughly explore this topic paying particular attention to the application of propiolic acid-derived Ugi adducts. The studied post-transformations include silver or cationic gold-catalyzed additions of various nucleophiles onto the propiolic acid-originated triple bond, palladium-catalyzed triple bond hydroarylations, intramolecular Diels-Alder reactions with the triple bond as dienophile and enolization-triggered cyclizations of the peptidyl position onto the triple bond.
In addition to post-Ugi chemistry, we have also explored a post-transformation potential of a metal-catalyzed three-component coupling of amine, aldehyde and alkyne (A3-coupling) that has been recently emerged as a key tool for the generation of various classes of propargylamines. While studying this topic, we have put a special emphasis on the exploration of processes involving additions of A3-coupling-derived secondary propargylamines to various (hetero)allenes and subsequent transition metal-catalyzed cyclizations. The key advantages of this strategy included remarkable catalyst- and substrate-based tunability and simple reaction settings. For example, we have developed a series of protocols relying on the additions of secondary propargylamines to isocyanates and subsequent selective conversion of the in situ generated propargylureas into imidazol-2-ones, imidazolidin-2-ones, oxazolidin-2-imines, pyrimidin-2-ones and benzo[d][1,3]diazepin-2-ones via silver-, gold- or palladium-catalyzed cyclizations.
The second research direction pursued by my group has eventually arisen from the first one when we have discovered a new class of aggregation-induced emission (AIE) luminophores 7 featuring boron complexes of 2-oxo-aldehyde-derived Ugi adducts. The Ugi adducts 6 contain inbuilt 1,3-dicarbonyl moiety bearing three bulky substituents that upon complexation with boron trifluoride diethyl etherate yields AIE-active O,O-chelated boron complexes 7. Such design makes these branched non-planar molecules non-emissive in dilute solutions. On the other hand, complexes 7 analogously to other AIE-luminophores start to emit in poor solvents or in solid state when the molecular aggregation occurs leading to the restriction of the intramolecular motion that is the main cause of nonradiative decay. To our delight, the solid-state quantum yields (QYs) for our novel AIEgens 7 were observed in the range of 0.80-1.00 setting the record for the boron-based solid-state emitters.
Publications
# denotes equal contribution; * denotes corresponding author(s)
Anatoly A. Peshkov, Olga Bakulina, Dmitry Dar’in, Grigory Kantin, Anton Bannykh, Vsevolod A. Peshkov, Mikhail Krasavin,* European Journal of Organic Chemistry, 2021, 1726–1731. Highlighted on a cover feature.
Rustam Zhumagambetov, Daniyar Kazbek,# Mansur Shakipov,# Daulet Maksut, Vsevolod A. Peshkov,* Siamac Fazli,* RSC Advances, 2020, 10, 45189–45198. Link to the database: cheml.io. Selected as a 2020 HOT RSC Advances article. Highlighted in RSC Advances Blog.
Yuqing Wang, Gaigai Wang, Anatoly A. Peshkov, Ruwei Yao, Muhammad Hasan, Manzoor Zaman, Chao Liu, Stepan Kashtanov, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Beilstein Journal of Organic Chemistry, 2020, 16, 1963–1973. This article is a part of the thematic issue "Organo-fluorine chemistry V".
Muhammad Hasan,# Manzoor Zaman,# Anatoly A. Peshkov,* Niyaz Amire, Adil Les, Anton A. Nechaev, Yuqing Wang, Stepan Kashtanov, Erik V. Van der Eycken, Olga P. Pereshivko, Vsevolod A. Peshkov,* European Journal of Organic Chemistry, 2020, 3378–3389. Highlighted on a cover feature.
Jing Gong, Anatoly Peshkov, Jiafeng Yu, Sagadat Amandykova, Aidana Gimnkhan, Jianjun Huang, Stepan Kashtanov, Olga P. Pereshivko,* Vsevolod A. Peshkov,* RSC Advances, 2020, 10, 10113–10117.
Manzoor Zaman,# Muhammad Hasan,# Anatoly Peshkov, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Advanced Synthesis & Catalysis, 2020, 362, 261–268.
Xiaochen Du, Jiafeng Yu, Jing Gong, Manzoor Zaman, Olga P. Pereshivko,* Vsevolod A. Peshkov,* European Journal of Organic Chemistry, 2019, 2502–2507.
Jianjun Huang, Yingchun Wang, Kristof Van Hecke, Olga P. Pereshivko,* Vsevolod A. Peshkov,* European Journal of Organic Chemistry, 2019, 2490–2497.
Chao Liu, Gaigai Wang, Yuqing Wang, Olga P. Pereshivko,* Vsevolod A. Peshkov,* European Journal of Organic Chemistry, 2019, 1981–1985. Highlighted on a front cover.
Mustafa Z. Kazancioglu,* Erbay Kalay, Elif Akin Kazancioglu, Vsevolod A. Peshkov, ChemistrySelect, 2019, 4, 8797–8799.
Xiaochen Du,# Jianjun Huang,# Anton A. Nechaev, Ruwei Yao, Jing Gong, Erik V. Van der Eycken, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Beilstein Journal of Organic Chemistry, 2018, 14, 2572–2579.
Chao Liu,# Gaigai Wang,# Yingchun Wang, Kristof Van Hecke, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Tetrahedron Letters, 2018, 59, 1823–1827. Highlighted on a front cover.
Vsevolod A. Peshkov,* Olga P. Pereshivko,* Anton A. Nechaev, Anatoly A. Peshkov, Erik Van der Eycken,* Chemical Society Reviews, 2018, 47, 3861–3898. Highlighted on a front cover.
Anton A. Nechaev, Kristof Van Hecke, Manzoor Zaman, Stepan Kashtanov, Liviu Ungur, Olga P. Pereshivko, Vsevolod A. Peshkov,* Erik Van der Eycken,* The Journal of Organic Chemistry, 2018, 83, 8170−8182.
Huiping Wei,# Gaigai Wang,# Yingchun Wang, Binbin Li, Jianjun Huang, Stepan Kashtanov, Kristof Van Hecke, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Chemistry an Asian Journal, 2017, 12, 825–829. Assigned as a VIP (very important paper) by the journal. Highlighted in ChemViews and on an inside cover.
Gaigai Wang, Chao Liu, Binbin Li, Yingchun Wang, Kristof Van Hecke, Erik Van der Eycken, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Tetrahedron, 2017, 73, 6372–6380.
Jianjun Huang,# Xiaochen Du,# Kristof Van Hecke, Erik Van der Eycken, Olga P. Pereshivko,* Vsevolod A. Peshkov,* European Journal of Organic Chemistry, 2017, 4379–4388. Assigned as a VIP (very important paper) by the journal.
Anton A. Nechaev, Anatoly A. Peshkov, Vsevolod A. Peshkov,* Erik V. Van der Eycken,* European Journal of Organic Chemistry, 2017, 1063–1069.
Huiping Wei,# Gaigai Wang,# Binbin Li, Jianjun Huang, Haiyan Li, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Heterocyclic Communications, 2016, 22, 333–337.
Matthew G. LaPorte,* Zhuzhu Wang, Raffaele Colombo, Atefeh Garzan, Vsevolod A. Peshkov, Mary Liang, Paul A. Johnston, Mark E. Schurdak, Malabika Sen, Daniel P. Camarco, Yun Hua, Netanya I. Pollock, John S. Lazo, Jennifer R. Grandis, Peter Wipf,* Donna M. Huryn,* Bioorganic & Medicinal Chemistry Letters, 2016, 26, 3581–3585.
Anton A. Nechaev,# Anatoly A. Peshkov,# Vsevolod A. Peshkov,* Erik V. Van der Eycken,* Synthesis, 2016, 48, 2280–2286.
Binbin Li, Steven Nguyen, Jianjun Huang, Gaigai Wang, Huiping Wei, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Tetrahedron Letters, 2016, 57, 1958–1962.
Huiping Wei,# Binbin Li,# Gaigai Wang, Kristof Van Hecke, Olga P. Pereshivko,* Vsevolod A. Peshkov,* Synthesis, 2016, 48, 1734–1740.
Celeste Alverez, Stacie L. Bulfer, Ramappa Chakrasali, Michael S. Chimenti, Raymond J. Deshaies, Neal Green, Mark Kelly, Matthew G. LaPorte, Taber S. Lewis, Mary Liang, William J. Moore, R. Jeffrey Neitz, Vsevolod A. Peshkov, Michael A. Walters, Feng Zhang, Michelle R. Arkin,* Peter Wipf,* Donna M. Huryn,* ACS Medicinal Chemistry Letters, 2016, 7, 182–187.
Binbin Li,# Huiping Wei,# Haiyan Li, Olga P. Pereshivko, Vsevolod A. Peshkov,* Tetrahedron Letters, 2015, 56, 5231–5234.
Anatoly A. Peshkov, Vsevolod A. Peshkov,* Olga P. Pereshivko, Kristof Van Hecke, Rakesh Kumar, Erik V. Van der Eycken,* The Journal of Organic Chemistry, 2015, 80, 6598–6608.
Anatoly A. Peshkov, Anton A. Nechaev, Olga P. Pereshivko, Jan L. Goeman, Johan Van der Eycken, Vsevolod A. Peshkov,* Erik V. Van der Eycken,* European Journal of Organic Chemistry, 2015, 4190–4197.
Tran Thi Thu Trang,# Anatoly A. Peshkov,# Jeroen Jacobs, Luc Van Meervelt, Vsevolod A. Peshkov,* Erik V. Van der Eycken,* Tetrahedron Letters, 2015, 56, 2882–2886.
Anatoly A. Peshkov, Vsevolod A. Peshkov,* Olga P. Pereshivko, Erik V. Van der Eycken,* Tetrahedron, 2015, 71, 3863–3871.
Anatoly A. Peshkov, Vsevolod A. Peshkov,* Zhenghua Li, Olga P. Pereshivko, Erik V. Van der Eycken,* European Journal of Organic Chemistry, 2014, 6390–6393.
Vsevolod A. Peshkov,* Anatoly A. Peshkov, Olga P. Pereshivko, Kristof Van Hecke, Lali L. Zamigaylo, Erik V. Van der Eycken, Nikolay Yu. Gorobets,* ACS Combinatorial Science, 2014, 16, 535–542.
Olga P. Pereshivko, Vsevolod A. Peshkov,* Anatoly A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Erik V. Van der Eycken,* Organic & Biomolecular Chemistry, 2014, 12, 1741–1750.
Olga P. Pereshivko,# Vsevolod A. Peshkov,# Jeroen Jacobs, Luc Van Meervelt, Erik V. Van der Eycken,* Advanced Synthesis & Catalysis, 2013, 355, 781–789.
Olga P. Pereshivko,# Vsevolod A. Peshkov,# Denis S. Ermolat’ev, Erik V. Van der Eycken,* Synlett, 2013, 24, 351–354. Highlighted in Synfacts, 2013, 9, 375.
Vsevolod A. Peshkov, Olga P. Pereshivko, Erik V. Van der Eycken,* Advanced Synthesis & Catalysis, 2012, 354, 2841–2848.
Nigam M. Mishra, Vsevolod A. Peshkov, Olga P. Pereshivko, Sachin G. Modha, Erik V. Van der Eycken,* Tetrahedron Letters, 2012, 53, 4676–4678.
Vsevolod A. Peshkov, Olga P. Pereshivko, Erik V. Van der Eycken,* Chemical Society Reviews, 2012, 41, 3790–3807.
Vsevolod A. Peshkov, Olga P. Pereshivko, Sofie Van Hove, Denis S. Ermolat'ev,* Erik V. Van der Eycken,* Synthesis, 2011, 3371–3374.
Vsevolod A. Peshkov, Olga P. Pereshivko, Sweta Sharma, Thirumal Meganathan, Virinder S. Parmar, Denis S. Ermolat'ev,* Erik V. Van der Eycken,* The Journal of Organic Chemistry, 2011, 76, 5867–5872.
Olga P. Pereshivko, Vsevolod A. Peshkov, Denis S. Ermolat'ev,* Sofie Van Hove, Kristof Van Hecke, Luc Van Meervelt, Erik V. Van der Eycken,* Synthesis, 2011, 1587–1594.
Vsevolod A. Peshkov, Sofie Van Hove, Pavel A. Donets, Olga P. Pereshivko, Kristof Van Hecke, Luc Van Meervelt, Erik V. Van der Eycken,* European Journal of Organic Chemistry, 2011, 1837–1840.
Vsevolod A. Peshkov, Olga P. Pereshivko, Pavel A. Donets, Vaibhav P. Mehta, Erik V. Van der Eycken,* European Journal of Organic Chemistry, 2010, 4861–4867.
Olga P. Pereshivko, Vsevolod A. Peshkov, Erik V. Van der Eycken,* Organic Letters, 2010, 12, 2638–2641.
