Nickel‐Catalyzed Reductive Coupling of Vinyl Triflates and 1,4‐Dicyanobenzene to Access Alkenyl Nitriles

Abstract

We report a vinyl cyanation reaction of vinyl triflates and readily available 1,4‐dicyanobenzene through a nickel‐catalyzed reductive coupling process. The reaction is operated under mild conditions with remarkable functional‐group compatibility. Cyclic vinyl triflates with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility is demonstrated by the derivatization of pharmaceutical and natural compounds, a scale‐up synthesis, and various functional group transformations. Preliminary mechanistic studies demonstrate that vinyl triflates are more reactive than 1,4‐dicyanobenzene towards the oxidative addition to nickel catalyst.