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

• Roman Yu. Peshkov,
• Elena V. Panteleeva,
• Wang Chunyan,
• Evgeny V. Tretyakov and
• Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

• Avenue, 9, Novosibirsk, 630090, Russia Natural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia Heilongjang University, Xuefu Road, 74, Harbin, 150080, China 10.3762/bjoc.12.153 Abstract A convenient one-pot approach to alkylcyanobiaryls is described. The

• , 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. Keywords: alkylcyanobiaryls; cross

• Discussion The suggested one-pot synthesis of alkylcyanobiaryls 5 comprises consecutive generation of terephthalonitrile dianion (12–) [30][31][32] by the addition of metallic sodium to a suspension of dinitrile 1 in liquid ammonia, treating of the thus formed 12− salt with a twofold excess of nitrile 2