Cyanomethylation of Substituted Fluorenes and Oxindoles with Alkyl Nitriles.

The first example of metal-free cyanomethylenation from alkyl nitriles of sp3 C-H bonds to afford quaternary carbon centers is described. This oxidative protocol is operationally simple and features good functional group compatibility. This method provides a novel approach to highly functionalized fluorene and oxindole derivatives, which are commonly used in material and pharmaceutical areas. Control experiments provide evidence of a radical reaction process.