C 47 Charushin, V. N. Nucleophilic aromatic substitution of hydrogen and related reactions [Electronic resource] / V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2007. - Vol. 17, № 5. - P249-254 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 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. \\\\Expert2\\nbo\\Mendeleev Communications\\2007, v.17, p.249.pdf |
H 19 Halogenation of Fluorinated 1,3-Dicarbonyl and 1,3,5-Tricarbonyl Compounds [Text] : доклад, тезисы доклада / D. V. Sevenard [и др.] // 18th ISFC international Symposium on Fluorine Chemistry. Bremen, 30th Jul.-4 Aug. 2006 г. : Final Program. Abstracts. - Bremen, 2006. - P271 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HALOGEN -- HALOGENATION AGENTS |
A 10 A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline / P. A. Slepukhin, V. I. Batalov, D. G. Kim, V. N. Charushin // Journal of Structural Chemistry. - 2012. - Vol.53, №1. - С. 145-150 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 8-ALLYLTHIOQUINOLINE -- X-RAY DIFFRACTION -- HALOGEN Аннотация: The reaction products of 8-allylthioquinoline with mercury halides are studied by single crystal X-ray diffraction. It is shown that the products are organomercury derivatives of salts of 2,3-dihydro[1,4]-thiazino[2,3,4-ij]quinoliniuim \\\\Expert2\\nbo\\Journal of Structural Chemistry\\2012, V. 53, N 1, p.145-150.pdf |
L 79 Lipunova, G. N. Fluorinated Quinolines: Synthesis, Properties and Applications / G. N. Lipunova, E. V. Nosova, V. N. Charushin // Fluorine in Heterocyclic Chemistry : Издательство "Springer", 2014. - Vol. 2. - С. 59-109. - Bibliogr. : p. 108-109 (158 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): fLUORINATED QUINOLINES -- SYNTHETIC METHODS -- CYCLOADDITION REACTIONS Аннотация: The data on the chemistry of fluorinated quinolines available in the literature of the last 10–15 years are presented. A variety of synthetic methods exploiting cyclization and cycloaddition reactions, displacements of halogen atoms or the diaza group, as well as direct fluorinations have been considered. Novel approaches to functionalization of polyfluorinated quinolines, including nucleophilic displacement of fluorine atoms, cross-coupling reactions, and synthesis on the basis of organometallic compounds are discussed. Selected representative examples of fluoroquinolines exhibiting a remarkable biological activity or those quinolines which have already found their applications in medicine will also be discussed in the text. The bibliography |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
C 57 Chupakhin, O. N. Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions / O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin // Green Chemistry. - 2017. - Vol. 19, № 13. - P2931-2935 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp2)–H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has first been carried out under electrochemical oxidative conditions. This versatile method for C–C bond formation between two aryl fragments can be realized under very mild potential-controlled oxidative conditions, and it does require neither incorporation of any halogen atoms or other leaving groups, nor the use of metal catalysts. The use of the electrochemical SHN methodology for modification of azaaromatic compounds has first been demonstrated. \\\\Expert2\\NBO\\Green Chemistry\\2017 v.19 p.2931-2935.pdf |
Chupakhin, O. N. Application of electrochemical oxidative methods in the C(SP2)–H functionalization of heterocyclic compounds / O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin // Advances in heterocyclic chemistry. - 2020. - Т. 131. - P1-47 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): C-H FUNCTIONALIZATION -- ELECTROCHEMICAL OXIDATION -- GREEN CHEMISTRY -- OCDC -- SN H REACTIONS Аннотация: New atom-economic and environmentally friendly processes should replace the traditional ways of building C–C, C–N, C–O, C–P, C–S bonds, which are usually based on the replacement of a halogen atom, and, therefore, required the preliminary modification of substrates, and the use of aggressive reagents, harsh conditions or expensive catalysts. In recent years, the direct metal-free functionalization of the C(sp2)–H bond, which provides the most efficient and low-waste pathway for molecular transformation, has attracted increasing attention. However, these transformations usually require stoichiometric amounts of chemical oxidizing agents. The modern world and its sustainable development trends are forcing the chemical industry to improve in an environmentally friendly direction and meet the requirements of “green chemistry.” In this regard, the use of electrochemical methods is extremely important. Electrochemical anodic oxidation is an ideal option for the replacement of chemical oxidizers in C–H functionalization reactions. The data on the main electrochemical methods and approaches used for the direct functionalization of the C(sp2)–H bond in heterocyclic compounds are classified and summarized in this paper. |