Catalytic Hydrocyanation of Activated Terminal Alkynes

Abstract A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β‐substituted acrylonitriles bearing an electron‐withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4‐diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E , Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.