Details

Autor(en) / Beteiligte

• Tejedor, David
• Delgado‐Hernández, Samuel
• Colella, Lucía
• García‐Tellado, Fernando

Titel

Catalytic Hydrocyanation of Activated Terminal Alkynes

Ist Teil von

• Chemistry : a European journal, 2019-11, Vol.25 (66), p.15046-15049

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Simplicity matters: A simple catalytic manifold using 1,4‐diazabicyclo[2.2.2]octane (DABCO) as the catalyst and acetone cyanohydrin as the cyanide source performs the hydrocyanation of terminal activated alkynes with high efficiency (see scheme). The catalytic manifold operates under the reactivity principle “a good nucleophile generates a strong base” and tolerates a diverse array of activating groups on the alkyne.