A Versatile One-Pot Access to Cyanoarenes from ortho- and para-Quinones: Paving the Way for Cyanated Functional Materials

Chemistry. 2016 Apr 4;22(15):5173-80. doi: 10.1002/chem.201600004. Epub 2016 Mar 1.

Abstract

A generally applicable direct synthesis of cyanoarenes from quinones is presented. Particular emphasis is placed on the preparation of precursors and target molecules relevant for organic materials, including halogenated cyanoarenes and larger cyanated acenes. The reaction and work-up protocols are adjusted for the challenges presented by the different substrates and products. Screening results of the initial reaction optimization are given to further facilitate adaptation to other synthetic problems. The universality of the reaction is finally highlighted by successful substitution of para-quinones by an ortho-quinone as the starting material.

Keywords: arenes; cyanides; fused-ring systems; quinones; reductive aromatization.

Publication types

  • Research Support, Non-U.S. Gov't