One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling
A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromid...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2016-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.12.153 |
| _version_ | 1818413035718443008 |
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| author | Roman Yu. Peshkov Elena V. Panteleeva Wang Chunyan Evgeny V. Tretyakov Vitalij D. Shteingarts |
| author_facet | Roman Yu. Peshkov Elena V. Panteleeva Wang Chunyan Evgeny V. Tretyakov Vitalij D. Shteingarts |
| author_sort | Roman Yu. Peshkov |
| collection | DOAJ |
| description | A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromides. The reaction is compatible with benzonitriles that contain methyl, methoxy and phenyl groups, fluorine atoms, and a 1-cyanonaphthalene residue. The variety of ω-substituted alkyl bromides, including an extra bromine atom, a double bond, cyano and ester groups, as well as a 1,3-dioxane fragment are suitable as alkylation reagents. |
| first_indexed | 2024-12-14T10:56:48Z |
| format | Article |
| id | doaj.art-459be92395bd462daefb6296c44b8c6a |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T10:56:48Z |
| publishDate | 2016-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-459be92395bd462daefb6296c44b8c6a2022-12-21T23:04:54ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972016-07-011211577158410.3762/bjoc.12.1531860-5397-12-153One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-couplingRoman Yu. Peshkov0Elena V. Panteleeva1Wang Chunyan2Evgeny V. Tretyakov3Vitalij D. Shteingarts4Laboratory of the Investigation of Nucleophilic and Radical Ionic Reactions, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 9, Novosibirsk, 630090, RussiaLaboratory of the Investigation of Nucleophilic and Radical Ionic Reactions, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 9, Novosibirsk, 630090, RussiaNatural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, RussiaLaboratory of the Investigation of Nucleophilic and Radical Ionic Reactions, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 9, Novosibirsk, 630090, RussiaLaboratory of the Investigation of Nucleophilic and Radical Ionic Reactions, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Avenue, 9, Novosibirsk, 630090, RussiaA convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromides. The reaction is compatible with benzonitriles that contain methyl, methoxy and phenyl groups, fluorine atoms, and a 1-cyanonaphthalene residue. The variety of ω-substituted alkyl bromides, including an extra bromine atom, a double bond, cyano and ester groups, as well as a 1,3-dioxane fragment are suitable as alkylation reagents.https://doi.org/10.3762/bjoc.12.153alkylcyanobiarylscross-couplingcyanoarenesreactive intermediatesreductive alkylation |
| spellingShingle | Roman Yu. Peshkov Elena V. Panteleeva Wang Chunyan Evgeny V. Tretyakov Vitalij D. Shteingarts One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling Beilstein Journal of Organic Chemistry alkylcyanobiaryls cross-coupling cyanoarenes reactive intermediates reductive alkylation |
| title | One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling |
| title_full | One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling |
| title_fullStr | One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling |
| title_full_unstemmed | One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling |
| title_short | One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling |
| title_sort | one pot synthesis of 4 alkyl 4 cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross coupling |
| topic | alkylcyanobiaryls cross-coupling cyanoarenes reactive intermediates reductive alkylation |
| url | https://doi.org/10.3762/bjoc.12.153 |
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