A Novel Cyanation Reaction of Arenes Using Acetonitrile as a Cyano Source

Shen et al. have reported a novel cyanation reaction of arenes using acetonitrile as a cyano source. According to their results, the reaction proceeds through a tandem process producing aryl iodides (1) from a copper complex catalyst-promoted iodination of simple arenes with N-iodosuccinimide (NIS), and a subsequent cyanation reaction. In this reaction, it is presumed that the cyano source is generated via the formation of an acetonitrile-derived cyanomethyl group-substituted TEMPO intermediate (2) and a sequential C-CN bond cleavage by the action of copper complex catalysts and hexamethyldisilane. This cyanation-process using TEMPO, copper complex catalysts and acetonitrile as a cyano source is a safe and inexpensive synthetic method and its future development can be expected.