Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 66, Pages 15046-15049Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903402
Keywords
acetone cyanohydrin; DABCO; hydrocyanation; organocatalysis; terminal alkynes
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Funding
- Spanish Ministry of Economy and Competitiveness (MINECO) [CTQ2015-63894-P, PGC2018-094503-B-C21]
- Agencia Estatal de Investigacin (AEI) [CTQ2015-63894-P, PGC2018-094503-B-C21]
- European Regional Development Funds (ERDF) [CTQ2015-63894-P, PGC2018-094503-B-C21]
- Spanish Ministry of Science, Innovation and Universities (MICINN) [CTQ2015-63894-P, PGC2018-094503-B-C21]
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A universal, practical and scalable organocatalytic hydrocyanation manifold to provide beta-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.
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