Electrochemical C−H Cyanation of Electron‐Rich (Hetero)Arenes. Issue 44 (10th July 2018)

• Record Type: Journal Article
• Authors: Hayrapetyan, Davit; Rit, Raja K.; Kratz, Markus; Tschulik, Kristina; Gooßen, Lukas J.
• Is Part Of: Chemistry. Volume 24:Issue 44(2018)
• Page Start: 11288
• Page End: 11291
• Publication Date: 2018-07-10
• Subjects: aromatic substitution -- cyanides -- electrochemistry -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201802247
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A straightforward method for the electrochemical C−H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochemical cell is reported. The platinum electrodes are passivated by adsorbed cyanide, which allows conversion of an exceptionally broad range of electron‐rich substrates all the way down to dialkyl arenes. The cyanide electrolyte can be replenished with HCN, opening opportunities for salt‐free industrial C−H cyanation. Abstract : Aromatic substitution : The electrochemical C−H cyanation of arenes is shown to constitute an advantageous synthetic alternative to traditional, waste‐intensive cyanation methods. It gives high yields by using simple, undivided electrochemical cells equipped with platinum‐sheet electrodes, proceeds well even in the presence of air and moisture, and allows waste‐free regeneration of the electrolyte (see scheme).