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

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.