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Mendeleev Communications, 2007, Volume 17, Issue 5, Pages 249–254
DOI: https://doi.org/10.1016/j.mencom.2007.09.001
(Mi mendc3448)
 

This article is cited in 78 scientific papers (total in 78 papers)

Nucleophilic aromatic substitution of hydrogen and related reactions

V. N. Charushinab, O. N. Chupakhinab

a Department of Organic Chemistry, Urals State Technical University, Ekaterinburg, Russian Federation
b I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
Abstract: The classical concept of nucleophilic aromatic substitution (SNAripso) has been complemented with a new synthetic methodology (SNH), enabling one to build new carbon–carbon C(sp2)–C(sp3), C(sp2)–C(sp2) and C(sp2)–C(sp) or carbon–heteroatom C(sp2)–X (X is O, N, P, S, halogen) bonds through nucleophilic displacement of hydrogen in an aromatic ring.
Document Type: Article
Language: English


Citation: V. N. Charushin, O. N. Chupakhin, “Nucleophilic aromatic substitution of hydrogen and related reactions”, Mendeleev Commun., 17:5 (2007), 249–254
Linking options:
  • https://www.mathnet.ru/eng/mendc3448
  • https://www.mathnet.ru/eng/mendc/v17/i5/p249
  • This publication is cited in the following 78 articles:
    1. Kseniya O. Khrapova, Pavel A. Volkov, Anton A. Telezhkin, Alexander I. Albanov, Oleg N. Chupakhin, Boris A. Trofimov, “Catalyst- and solvent-free regiospecific SNHAr phosphinylation of pyridines with H-phosphinates mediated by benzoylphenylacetylene”, Org. Biomol. Chem., 22:26 (2024), 5419  crossref
    2. Kseniya V. Belyaeva, Lina P. Nikitina, Ludmila A. Oparina, Veronika S. Saliy, Denis N. Tomilin, Anton V. Kuzmin, Andrei V. Afonin, Boris A. Trofimov, “Catalyst-free nucleophilic substitution of hydrogen in quinoline rings by acylethynylpyrroles: stereoselective synthesis of 2-(E-2-acylethenylpyrrolyl)quinolines”, New J. Chem., 48:3 (2024), 1336  crossref
    3. Valery N. Charushin, Mikhail V. Varaksin, Egor V. Verbitskiy, Oleg N. Chupakhin, Advances in Heterocyclic Chemistry, 144, 2024, 1  crossref
    4. V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125  mathnet  mathnet  crossref  isi  scopus
    5. A. A Telezhkin, P. A Volkov, K. O Khrapova, “Nucleophilic substitution of hydrogen in pyridine and its derivatives by organophosphorus nucleophiles in the presence of electron-deficient acetylenes”, Žurnal organičeskoj himii, 59:10 (2023), 1269  crossref
    6. S. G. Zlotin, K. S. Egorova, V. P. Ananikov, A. A. Akulov, M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. P. Bryliakov, A. D. Averin, I. P. Beletskaya, E. L. Dolengovski, Yu. H. Budnikova, O. G. Sinyashin, Z. N. Gafurov, A. O. Kantyukov, D. G. Yakhvarov, A. V. Aksenov, M. N. Elinson, V. G. Nenajdenko, A. M. Chibiryaev, N. S. Nesterov, E. A. Kozlova, O. N. Mart'yanov, I. A. Balova, V. N. Sorokoumov, D. A. Guk, E. K. Beloglazkina, D. A. Lemenovskii, I. Yu. Chukicheva, L. L. Frolova, E. S. Izmest'ev, I. A. Dvornikova, A. V. Popov, A. V. Kutchin, D. M. Borisova, A. A. Kalinina, A. M. Muzafarov, I. V. Kuchurov, A. L. Maksimov, A. V. Zolotukhina, “The green chemistry paradigm in modern organic synthesis”, Russian Chem. Reviews, 92:12 (2023), RCR5104  mathnet  mathnet  crossref  isi  scopus
    7. Alexey A. Akulov, Mikhail V. Varaksin, Pieter Mampuys, Valery N. Charushin, Oleg N. Chupakhin, Bert U. W. Maes, “C(sp2)–H functionalization in non-aromatic azomethine-based heterocycles”, Org. Biomol. Chem., 19:2 (2021), 297  crossref
    8. Boris V. Lyalin, Vera L. Sigacheva, Anastasia S. Kudinova, Sergey V. Neverov, Vladimir A. Kokorekin, Vladimir A. Petrosyan, “Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds”, Molecules, 26:16 (2021), 4749  crossref
    9. Hongjian Wang, Yonghong Ruan, Yu-Mei Lin, Haiping Xia, “Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate”, Chem. Sci., 12:18 (2021), 6315  crossref
    10. A. V. Shchepochkin, F. V. Antipin, V. N. Charushin, O. N. Chupakhin, “Oxidative C–H Functionalization of Arenes: Main Tool of 21st Century Green Chemistry. A Review”, Dokl Chem, 499:1 (2021), 123  crossref
    11. Pavel A. Volkov, Anton A. Telezhkin, Kseniya O. Khrapova, Nina I. Ivanova, Alexander I. Albanov, Nina K. Gusarova, Boris A. Trofimov, “Metal-free SHN cross-coupling of pyridines with phosphine chalcogenides: polarization/deprotonation/oxidation effects of electron-deficient acetylenes”, New J. Chem., 45:14 (2021), 6206  crossref
    12. Boris A. Trofimov, Pavel A. Volkov, Anton A. Telezhkin, “Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles”, Molecules, 26:22 (2021), 6824  crossref
    13. Ergin Keleş, Burcu Ayd{\i}ner, Yahya Nural, Nurgül Seferoğlu, Ertan Şahin, Zeynel Seferoğlu, “A new mechanism for selective recognition of cyanide in organic and aqueous solution”, Eur J Org Chem, 2020:30 (2020), 4681  crossref
    14. Igor L. Dalinger, Alexandr V. Kormanov, Tatyana K. Shkineva, Aleksei B. Sheremetev, “Reactivity of Azasydnones: Unusual Diversity in Reactions of Chloro‐ and Nitrophenyl Derivatives with Nitrogen Nucleophiles”, Asian J Org Chem, 9:5 (2020), 811  crossref
    15. Yuriy A. Kvashnin, Egor V. Verbitskiy, Ekaterina F. Zhilina, Gennady L. Rusinov, Oleg N. Chupakhin, Valery N. Charushin, “Synthesis of Heteroannulated Indolopyrazines through Domino N–H Palladium-Catalyzed/Metal-Free Oxidative C–H Bond Activation”, ACS Omega, 5:25 (2020), 15681  crossref
    16. Pieter Mampuys, Timofey D. Moseev, Mikhail V. Varaksin, Johan De Houwer, Christophe M. L. Vande Velde, Oleg N. Chupakhin, Valery N. Charushin, Bert U. W. Maes, “Synthesis of Functionalized Pyrazin-2(1H)-ones via Tele-Nucleophilic Substitution of Hydrogen Involving Grignard Reactants and Electrophiles”, Org. Lett., 21:8 (2019), 2699  crossref
    17. Igor L. Dalinger, Olga V. Serushkina, Dmitry L. Lipilin, Aleksei A. Anisimov, Kyrill Yu. Suponitsky, Aleksei B. Sheremetev, “Nitration of Azasydnones and Azasydnonimines: A Method for the Functionalization of Aryl Derivatives”, ChemPlusChem, 84:7 (2019), 802  crossref
    18. Konstantin L. Obydennov, Tatiana V. Glukhareva, “Synthesis and properties of bi- and tricyclic 1,3-thiazoline/thiazolidine assemblies linked by an exocyclic S=S double bond”, Chem Heterocycl Comp, 55:11 (2019), 1013  crossref
    19. V. N. Charushin, O. N. Chupakhin, “Nucleophilic C—H functionalization of arenes: a contribution to green chemistry”, Russ Chem Bull, 68:3 (2019), 453  crossref
    20. A. A. Rempel, A. A. Valeeva, “Nanostructured titanium dioxide for medicinal chemistry”, Russ Chem Bull, 68:12 (2019), 2163  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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