Low-Toxic Electrophilic Cyanating Reagent

　Dimethylmalononitrile (1) is a low-toxic electrophilic cyanating reagent and can introduce cyano groups into aromatic rings.^1,2) Aryl Grignard reagents (ArMgX) or aryllithiums (ArLi), derived from aryl halides (ArX), react with 1 to give cyano compounds (ArCN) in good yields. This reaction can be conducted under a transition metal free condition, and is applicable for various types of heteroaromatic or sterically hindered substrates. As cyano groups can be converted to other functional groups or scaffolds, further applications are anticipated to be reported.