№ 103 Лаборатория эффективного катализа (ЛЭК)

 

https://www.chemcatgroup.com/research-chemcatgroup

 

Заведующий лабораторией: д.х.н. Чусов Денис Александрович
(тел. +7(499)135-9291, e-mail )

 

Сотрудники лаборатории

к.х.н. Абрамова Н.В., к.х.н. Афанасьев О.И., д.х.н. Кузнецов Н.Ю., Модин А.А., к.х.н. Сафронов С.В., к.х.н. Фаткулин А.Р.

 

Аспиранты

Балалаева А.И., Козлов А.С.

 

Студенты

Клюев Ф.С., Зверева О.В., Болдырев А.Н., Смирнов И.В., Лосев М.А., Шандыбо М.А., Камалова А.В., Корочанцев В.А., Лебедева Н.Д., Прохоров А.В., Хайлук А.Д., Ракитянский Д.А.

 

Область исследований

Нашей группой предложена концепция восстановительного присоединения без внешнего источника водорода. Концепция заключается в использовании монооксида углерода в качестве восстанавливающего агента. В качестве источника водорода выступает один из реагентов (амин, амид, карбоновая кислота, СН-фрагмент). Избежав необходимости использования внешнего источника водорода, нам удалось создать методы, в которых не затрагиваются функциональные и защитные группы. Более того, удалось осуществить превращения, которые ранее не были возможны из-за гидрирования исходных реагентов. Подход также позволяет решить проблему утилизации угарного газа. Разрабатываемые подходы используются для синтеза лекарственных препаратов, природных соединений и препаратов для нужд агропромышленного комплекса.

Новые селективные реакции образования связей углерод-азот (получение аминов, амидов, гетероциклов) углерод-углерод (получение карбоновых кислот и их эфиров, нитрилов), углерод-кислород (получение простых и сложных эфиров).

Параллельно ведется разработка гомогенных и гетерогенных катализаторов и исследование их активности в реакциях образования связей углерод-углерод, углерод-азот, углерод-кислород.

А также создание новых активных каталитических систем путем модификации и усложнения структуры катализатора. Мы предлагаем активировать уже известные и доступные катализаторы с помощью простых добавок. В качестве таких активирующих добавок могут быть использованы фторид-анионы.

Коллектив группы весьма молодой и дружелюбный. Все аспиранты защищают диссертации в срок. В среднем суммарный импакт-фактор журналов у аспиранта, выполнившего диссертационное исследование в нашей группе, более 25.

 

Действующие гранты и контракты

• Грант РНФ № 24-43-00096 «Разработка фтор-содержащих бифункциональных катализаторов полимеризации» (Руководитель Чусов Д.А.)
  https://www.rscf.ru/project/24-43-00096/
• Грант РНФ № 22-73-10020 «Селективные реакции восстановительного аминирования» (Руководитель Афанасьев О.И.)
  https://www.rscf.ru/project/22-73-10020/
• Грант РНФ № 24-73-00162 «Восстановительные процессы с образованием C-N и С-С связей с использованием гипофосфита натрия» (Руководитель Подъячева Е.С.)
  https://www.rscf.ru/project/24-73-00162/

 

Список основных публикаций за 2014-2024 г.г.

1. Reductive Amination without an External Hydrogen Source
   D. Chusov, B. List
   Angew. Chem. Int. Ed., 2014, 53, 5199-5201 10.1002/anie.201400059 Impact Factor: 16.8
2. Atom- and Step-Economical Preparation of Reduced Knoevenagel Adducts Using CO as a Deoxygenative Agent
   P. N. Kolesnikov, D. L. Usanov, E. A. Barablina, V. I. Maleev, D. Chusov
   Org. Lett., 2014, 16, 19, 5068-5071 10.1021/ol502424t Impact Factor: 5.2
3. Ruthenium-Catalyzed Reductive Amination without an External Hydrogen Source
   P. N. Kolesnikov, N. Z. Yagafarov, D. L. Usanov, V. I. Maleev, D. Chusov
   Org. Lett., 2015, 17, 2, 173–175 10.1021/ol503595m Impact Factor: 5.2
4. Reductive Transformations of Carbonyl Compounds Catalyzed by Rhodium Supported on a Carbon Matrix by using Carbon Monoxide as a Deoxygenative Agent
   N. Z. Yagafarov, D. L. Usanov, A. P. Moskovets, N. D. Kagramanov, V. I. Maleev, D. Chusov
   ChemCatChem, 2015, 7, 2590–2593 10.1002/cctc.201500493 Impact Factor: 4.5
5. Cyclobutadiene Metal Complexes: A New Class of Highly Selective Catalysts. An Application to Direct Reductive Amination
   O. I. Afanasyev, A. A. Tsygankov, D. L. Usanov, D. S. Perekalin, N. V. Shvydkiy, V. I. Maleev, A. R. Kudinov, D. Chusov
   ACS Catal., 2016, 6, 3, 2043–2046 10.1021/acscatal.5b02916 Impact Factor: 12.9
6. Dichotomy of Reductive Addition of Amines to Cyclopropyl Ketones vs Pyrrolidine Synthesis
   O. I. Afanasyev, A.A. Tsygankov, D.L. Usanov, D. Chusov
   Org. Lett., 2016, 18, 22, 5968–5970 10.1021/acs.orglett.6b02945 Impact Factor: 5.2
7. The synthesis of sterically hindered amines by a direct reductive amination of ketones
   N. Z. Yagafarov, P. N. Kolesnikov, D. L. Usanov, V. V. Novikov, Y. V. Nelyubina, D. Chusov
   Chem. Commun., 2016, 52, 1397-1400 10.1039/C5CC08577B Impact Factor: 4.9
8. Reductive amination catalyzed by iridium complexes using carbon monoxide as a reducing agent
   P. Moskovets, D. L. Usanov, O. I. Afanasyev, V. A. Fastovskiy, A. P. Molotkov, K. M. Muratov, G. L. Denisov, S.S. Zlotskii, A. F. Smol'yakov, D. A. Loginov and D. Chusov
   Org. Biomol. Chem., 2017, 15, 6384–6387. 10.1039/C7OB01005B Impact Factor: 3.2
9. Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent
   Afanasyev O. I., Usanov D. L., Chusov D.
   Org. Biomol. Chem., 2017, 15, 10164–10166 10.1039/C7OB02795H Impact Factor: 3.2
10. Dichotomy of atom-economical hydrogen-free reductive amidation vs exhaustive reductive amination
    P. N. Kolesnikov, D. L. Usanov, K. M. Muratov, D. Chusov
    Org. Lett., 2017, 19, 5657–5660. 10.1021/acs.orglett.7b02821 Impact Factor: 5.2
11. Planar-chiral rhodium(III) catalyst with sterically demanding cyclopentadienyl ligand and its application for enantioselective synthesis of dihydroisoquinolones
    E. A. Trifonova, N. M. Ankudinov, A. A. Mikhaylov, D. A. Chusov, Y. V. Nelyubina, D. S. Perekalin
    Angew. Chem. Int. Ed., 2018, 57, 7714–7718 10.1002/anie.201801703 Impact Factor: 16.8
12. Formal reductive addition of acetonitrile to aldehydes and ketones
    Karim M Muratov, Ekaterina A. Kuchuk, Sreekumar Vellalath, Oleg I Afanasyev, Alexei P. Moskovets, Gleb L. Denisov, Denis Chusov
    Org. Biomol. Chem., 2018, 16, 7693 - 7701. 10.1039/C8OB01992D, Impact Factor: 3.2
13. Atom- and Step-Economical Ruthenium-Catalyzed Synthesis of Esters from Aldehydes or Ketones and Carboxylic Acids
    Sofiya A. Runikhina, Dmitry L. Usanov, Alexander O. Chizhov, Denis Chusov
    Org. Lett., 2018, 20, 24, 7856–7859. 10.1021/acs.orglett.8b03375, Impact Factor: 5.2
14. Anthracene rhodium complexes with metal coordination at the central ring – a new class of catalysts for reductive amination
    Ekaterina A. Kuchuk, Karim M Muratov, Dmitry Perekalin, Denis Chusov
    Org. Biomol. Chem., 2019, 17, 83—87. 10.1039/C8OB02561D, Impact Factor: 3.2
15. Aldehydes as alkylating agents for ketones
    Sofiya A. Runikhina, Oleg I. Afanasyev, Klim Biriukov, Dmitry S. Perekalin, Martin Klussmann, Denis Chusov
    Chem. Eur. J., 2019, 25, 71, 16225—16229. 10.1002/chem.201904605, Impact Factor: 4.3
16. Reductive Amination in the Synthesis of Pharmaceuticals
    Oleg I. Afanasyev, Ekaterina Kuchuk, Dmitry L. Usanov, Denis Chusov
    Chemical Reviews, 2019, 119, 23, 11857—11911. 10.1021/acs.chemrev.9b00383, Impact Factor: 51.4
17. Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst
    Alexey A. Tsygankov, Maria Makarova, Oleg I. Afanasyev, Alexey S Kashin, Alexander V Naumkin, Dmitry A Loginov, Denis Chusov
    ChemCatChem, 2020, 12, 1, 112—117. 10.1002/cctc.201901465, Impact Factor: 4.5
18. A Dual Threat: Redox‐Activity and Electronic Structures of Well‐Defined Donor–Acceptor Fulleretic Covalent‐Organic Materials
    G.A. Leith, A.M. Rice, B.J. Yarbrough, A.A. Berseneva, R.T. Ly, C.N. Buck, D. Chusov, A.J. Brandt, D.A. Chen, B.W. Lamm, M. Stefik, K.S. Stephenson, M.D. Smith, A.K. Vannucci, P.J. Pellechia, S. Garashchuk, N.B. Shustova
    Angew. Chem. Int. Ed., 2020, 59, 6000—6006. 10.1002/anie.201914233, Impact Factor: 16.8
19. Redox condensations of o-nitrobenzaldehydes with amines under mild conditions – total synthesis of the Vasicinone family
    Evgeniya Podyacheva, Oleg I. Afanasyev, Alexander Rudenko, Alexey A. Tsygankov, Maria Makarova, Denis Chusov
    Journal of Organic Chemistry, 2020, 85, 14, 9347–9360. 10.1021/acs.joc.0c00794, Impact Factor: 3.6
20. Osmium catalysis in the reductive amination using carbon monoxide as a reducing agent
    Mikhail M. Vinogradov, Oleg I. Afanasyev, Yulia V. Nelyubina, Gleb L. Denisov, Dmitry A. Loginov, Denis Chusov
    Molecular Catalysis, 2020, 498, 111260. 10.1016/j.mcat.2020.111260, Impact Factor: 4.6
21. Easy Access to Versatile Catalytic Systems for C-H Activation and Reductive Amination Based on Tetrahydrofluorenyl Rhodium(III) Complexes
    Vladimir B. Kharitonov, Sofiya A. Runikhina, Yulia V. Nelyubina, Dmitry V. Muratov, Denis Chusov, Dmitry Loginov
    Chem. Eur. J., 2021, 27, 10903-10912. 10.1002/chem.202100572, Impact Factor: 4.3
22. Carbon Monoxide-Driven Osmium Catalyzed Reductive Amination Harvesting WGSR Power
    Klim Biriukov, Mikhail M. Vinogradov, Oleg I. Afanasyev, Dmitry V. Vasilyev, Alexey A. Tsygankov, Maria Godovikova, Yulia V. Nelyubina, Dmitry A. Loginov, Denis Chusov
    Catalysis Science & Technology, 2021, 11, 4922 - 4930. 10.1039/D1CY00695A, Impact factor: 5.0
23. Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E-H Bonds
    Nikita M. Ankudinov, Denis A. Chusov, Yulia V. Nelyubina, Dmitry Perekalin
    Angew. Chem. Int. Ed., 2021, 60, 18712 - 18720. 10.1002/anie.202105179, Impact Factor: 16.8
24. Reductive aldol-type reactions in the synthesis of pharmaceuticals
    Sofiya Runikhina, Dmitry Eremin, Denis Chusov
    Chem. Eur. J., 2021, 27, 15327-15360. 10.1002/chem.202101768, Impact Factor: 4.3
25. Straightforward Access to High-Performance Organometallic Catalysts by Fluoride Activation: Proof of Principle on Asymmetric Cyanation, Asymmetric Michael Addition, CO2 Addition to Epoxide, and Reductive Alkylation of Amines by Tetrahydrofuran
    Alexey A. Tsygankov, Denis Chusov
    ACS Catal., 2021, 11, 21, 13077–13084. 10.1021/acscatal.1c03785, Impact Factor: 12.9
26. Enhancing the efficiency of the ruthenium catalysts in the reductive amination without an external hydrogen source
    Artemy R. Fatkulin, Oleg I. Afanasyev, Alexey A. Tsygankov, Denis Chusov
    Journal of Catalysis, 2022, 405, 404–409. 10.1016/j.jcat.2021.12.018, Impact Factor: 7.3
27. Syngas Instead of Hydrogen Gas as a Reducing Agent ─ A Strategy To Improve the Selectivity and Efficiency of Organometallic Catalysts
    Evgeniya Podyacheva, Oleg I. Afanasyev, Vladimir S. Ostrovskii, Denis Chusov
    ACS Catal., 2022, 12, 9, 5145–5154. 10.1021/acscatal.2c01000, Impact Factor: 12.9
28. Asymmetric cyclopropanation of electron-rich alkenes by the racemic diene rhodium catalyst: the chiral poisoning approach
    Evgeniya A Trifonova, Nikita M Ankudinov, Denis Chusov, Yulia V Nelyubina, Dmitry Perekalin
    Chem. Commun., 2022, 58, 6709-6712. 10.1039/D2CC01648F, Impact Factor: 4.9
29. Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters
    Evgeniya Podyacheva, Oleg I. Afanasyev, Dmitry V. Vasilyev, Denis Chusov
    ACS Catal., 2022, 12, 12, 7142–7198. 10.1021/acscatal.2c01133, Impact Factor: 12.9
30. Borrowing hydrogen amination: whether a catalyst is required?
    Andrey S. Kozlov Oleg I. Afanasyev, Denis Chusov
    Journal of Catalysis, 2022, 413, 1070-1076. 10.1016/j.jcat.2022.08.014, Impact Factor: 7.3
31. Osmium-catalyzed reductive processes: hydrogen transfer, hydrogen borrowing, hydrogenation, hydroformylation, reductive amination and water gas shift reaction
    Klim O. Biriukov, Oleg I. Afanasyev, Maria I. Godovikova, Dmitry A. Loginov, Denis A. Chusov
    Russ Chem Rev, 2022, 91, 9, RCR5045. 10.1070/RCR5045, Impact Factor: 7.7
32. Fluoride Additive as a Simple Tool to Qualitatively Improve Performance of Nickel-Catalyzed Asymmetric Michael Addition of Malonates to Nitroolefins
    Oleg I. Afanasyev, Fedor Kliuev, Alexey Tsygankov, Yulia Nelyubina, Evgenii Gutsul, Valentin Novikov, Denis Chusov
    Journal of Organic Chemistry, 2022; 87, 18, 12182-12195. 10.1021/acs.joc.2c01339, Impact Factor: 3.6
33. Sodium hypophosphite as a bulk and environmentally friendly reducing agent in the reductive amination
    Fedor Kliuev, Anton Kuznetsov, Oleg I. Afanasyev, Sofiya A. Runikhina, Ekaterina Kuchuk, Evgeniya Podyacheva, Alexey A. Tsygankov Denis Chusov
    Org. Lett., 2022, 24, 42, 7717–772. 10.1021/acs.orglett.2c02807, Impact Factor: 5.2
34. Sodium hypophosphite mediated reductive amination of carbonyl compounds with N,N-dialkylformamides
    Artemy R. Fatkulin, Vasily Korochantsev, Oleg I. Afanasyev, Evgeniya Podyacheva, Olga Chusova, Dmitry V. Muratov, Maria I. Godovikova, Sergei Semenov, Denis Chusov
    New Journal of Chemistry, 2023, 47, 6532-6535. 10.1039/D3NJ00728F, Impact Factor: 3.3
35. Catalytic utilization of converter gas – an industrial waste for the synthesis of pharmaceuticals
    Sofiya A. Runikhina, Oleg I. Afanasyev, Ekaterina A. Kuchuk, Dmitry S. Perekalin, Rajenahally V. Jagadeesh, Matthias Beller, Denis Chusov
    Chem. Sci., 2023, 14, 4346-4350. 10.1039/D3SC00257H, Impact Factor: 8.4
36. Syngas as a synergistic reducing agent for the selective reductive amination – a mild route to bioactive amines
    Evgeniya Podyacheva, Alexandra I. Balalaeva, Oleg I Afanasyev, Sofiya Runikhina, Olga Chusova, Andrey Kozlov, Saihu Liao, Denis Chusov
    New Journal of Chemistry, 2023, 47, 10514-10518. 10.1039/D3NJ01258A, Impact Factor: 3.3
37. A Pioneering Career in Catalysis: Henri B. Kagan
    Denis Chusov, Gary A. Molander, Virginie Ratovelomanana-Vidal, Olivier Riant, Emmanuelle Schulz
    ACS Catal., 2023, 13, 11494−11508. 10.1021/acscatal.3c02965, Impact Factor: 12.9
38. Peculiarities of fluoride activation of porphyrin and phthalocyanine catalysts by the example of zirconium and hafnium in the production of cyclic carbonates
    Klim O. Biriukov, Svetlana A. Belova, Semyon V. Dudkin, Oleg I. Afanasyev, Maria Godovikova, Denis Chusov
    Molecular Catalysis, 2023, 549, 113432. 10.1016/j.mcat.2023.113432, Impact Factor: 4.6
39. Streamlining the synthesis of amides using Nickel-based nanocatalysts
    Jie Gao, Rui Ma, Fairoosa Poovan, Lan Zhang, Hanan Atia, Narayana V. Kalevaru, Wenjing Sun, Sebastian Wohlrab, Denis A. Chusov, Ning Wang, Rajenahally V. Jagadeesh, Matthias Beller
    Nature Communications, 2023, 14, 5013. 10.1038/s41467-023-40614-1, Impact Factor: 16.6
40. Reductive coupling of nitroarenes with carboxylic acids – a direct route to amide synthesis
    Mikhail A. Losev, Andrey Kozlov, Vladimir B. Kharitonov, Oleg I Afanasyev, Fedor S. Kliuev, Natalya Khrushcheva, Ludmila A. Bulygina, Dmitry A Loginov and Denis Chusov
    Org. Biomol. Chem., 2023, 21, 8477–8481. 10.1039/D3OB01452E, Impact Factor: 3.2
41. Planar Chiral Rhodium Complex Based on the Tetrahydrofluorenyl Core for Enantioselective Catalysis
    Vladimir Kharitonov; Evgeniya Podyacheva, Denis Chusov, Yulia Nelyubina, Dmitry Muratov, Dmitry Loginov
    Org. Lett., 2023, ASAP. 10.1021/acs.orglett.3c03726, Impact Factor: 5.2
42. Simplified Version of the Eschweiler-Clarke Reaction
    Klim O. Biriukov, Evgeniya Podyacheva, Ignatii Tarabrin, Oleg I. Afanasyev, Denis Chusov
    Journal of Organic Chemistry, 2024, 89, 5, 3580–3584. 10.1021/acs.joc.3c02476, Impact Factor: 3.6
43. Air-Stable Arene Manganese Complexes as Catalysts for the Syngas-Assisted Direct Reductive Amination, Cyanation of Aldehyde, and CO2 Fixation by Epoxide with High Functional Groups Tolerance
    Ivan V. Smirnov, Klim O. Biriukov, Nikita V. Shvydkiy, Dmitry S. Perekalin, Oleg I. Afanasyev, and Denis Chusov
    The Journal of Organic Chemistry, 2024, 89, 14, 10338-10343. 10.1021/acs.joc.4c00842, Impact Factor: 3.6