Title: Catalytic Hydrocyanation of Activated Terminal Alkynes.
Authors: Tejedor, David; Delgado‐Hernández, Samuel; Colella, Lucía; García‐Tellado, Fernando
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.
Subjects: ALKYNES; ACRYLONITRILE; ISOMERS; CYANIDES; MANIFOLDS (Mathematics); ACETONE
Publication: Chemistry - A European Journal, 2019, Vol 25, Issue 66, p15046
ISSN: 0947-6539
Publication type: Academic Journal
DOI: 10.1002/chem.201903402

Catalytic Hydrocyanation of Activated Terminal Alkynes.

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