One-pot synthesis of 4 '-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling Full article
| Journal |
Beilstein Journal of Organic Chemistry
ISSN: 1860-5397 |
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| Output data | Year: 2016, Volume: 12, Pages: 1577-1584 Pages count : 8 DOI: 10.3762/bjoc.12.153 | ||||||
| Tags | alkylcyanobiaryls; cross-coupling; cyanoarenes; reactive intermediates; reductive alkylation | ||||||
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Abstract:
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 omega-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.
Cite:
Peshkov R.Y.
, Panteleeva E.V.
, Wang Chunyan
, Tretyakov E.V.
, Shteingarts V.D.
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. 2016.
V.12. P.1577-1584. DOI: 10.3762/bjoc.12.153
WOS
Scopus
РИНЦ
OpenAlex
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. 2016.
V.12. P.1577-1584. DOI: 10.3762/bjoc.12.153
WOS
Scopus
РИНЦ
OpenAlex
Files:
Full text from publisher
Dates:
| Published online: | Jul 25, 2016 |
Identifiers:
| Web of science: | WOS:000381255200001 |
| Scopus: | 2-s2.0-84979581751 |
| Elibrary: | 27095984 |
| OpenAlex: | W2480387551 |