title: One-pot synthesis of 4'-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling.
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 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.
authors: Laboratory 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, Russia; Natural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
authors: Roman Yu
authors: RY
authors: Peshkov
authors: Laboratory 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, Russia; Natural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
authors: Elena V
authors: EV
authors: Panteleeva
authors: Natural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia; Heilongjang University, Xuefu Road, 74, Harbin, 150080, China.
authors: Wang
authors: W
authors: Chunyan
authors: Laboratory 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, Russia; Natural Sciences Department, Novosibirsk State University, Pirogova St., 2, Novosibirsk, 630090, Russia.
authors: Evgeny V
authors: EV
authors: Tretyakov
authors: Laboratory 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, Russia.
authors: Vitalij D
authors: VD
authors: Shteingarts
keywords: alkylcyanobiaryls; cross-coupling; cyanoarenes; reactive intermediates; reductive alkylation