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Catalytic Hydrocyanation of Activated Terminal Alkynes

AuthorsTejedor, David ; Delgado-Hernández, Samuel; Colella, Lucía; García-Tellado, Fernando
KeywordsAcetone cyanohydrin
Terminal alkynes
Issue Date27-Nov-2019
CitationChemistry - A European Journal 25(66): 15046-15049 (2019)
AbstractA universal, practical and scalable organocatalytic hydrocyanation manifold to provide ß¿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.
Publisher version (URL)https://doi.org/10.1002/chem.201903402
Identifiersdoi: 10.1002/chem.201903402
e-issn: 1521-3765
issn: 0947-6539
Appears in Collections:(IPNA) Artículos
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