Beilstein Journal of Organic Chemistry (Jul 2016)

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,
  • Vitalij D. Shteingarts

DOI
https://doi.org/10.3762/bjoc.12.153
Journal volume & issue
Vol. 12, no. 1
pp. 1577 – 1584

Abstract

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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.

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