One-pot synthesis of 4 '-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

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

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

Authors

Peshkov Roman Yu. ^1,2 , Panteleeva Elena V. ^1,2 , Wang Chunyan ^2,3 , Tretyakov Evgeny V. ^1,2 , Shteingarts Vitalij D. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Lab Invest Nucleophil & Rad Ion React, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Pirogova St 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Heilongjang Univ, Xuefu Rd 74, Harbin 150080, Peoples R China

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.

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

Full text from publisher

Published online:

Jul 25, 2016

Web of science	WOS:000381255200001
Scopus	2-s2.0-84979581751
Elibrary	27095984
OpenAlex	W2480387551