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- Title
Nickel-catalyzed multicomponent coupling reaction using ynones.
- Authors
Arai, Takayoshi; Ikematsu, Yui; Suemitsu, Yuuki
- Abstract
Conjugate addition of Me3SiCN to ynones is smoothly catalyzed by Ni(cod)2 to give β-cyano-silyloxyallenes quantitatively. Subsequent treatment of the silyloxyallenes with N-bromo succinimide (NBS) provides the tetrasubstituted α-bromo-β-cyanoenones in high yields (up to 95 %) with excellent Z-selectivity (E/Z = up to >1/99). X-ray crystallographic analysis shows a bent structure of the α-bromo-β-cyanoenone due to deconjugation of the π-bond and the carbonyl group. Furthermore, three-component coupling reactions of ynones, dialkylzinc, and aldehydes are catalyzed by Ni(cod)2 to provide tetrasubstituted olefins.
- Subjects
SUCCINIMIDES; ALKENES; X-ray crystallography; MULTIPHASE flow; CRYSTALLOGRAPHY; COUPLING agents (Chemistry)
- Publication
Pure & Applied Chemistry, 2010, Vol 82, Issue 7, p1485
- ISSN
0033-4545
- Publication type
Article
- DOI
10.1351/PAC-CON-09-09-08