Metal-catalysed carbon-carbon bond formation in the reaction of malononitrile with β-dicarbonyls

Nickel acetylacetonate effectively catalyses the carbon-carbon bond formation between malononitrile and β-dicarbonyls. In these metal-catalysed reactions malononitrile behaves as an electrophile towards the intercarbonylic carbon, so exhibiting a reverse reactivity compared with that one under basic...

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Bibliographic Details
Published in:Journal of molecular catalysis. A, Chemical Chemical, 1997-10, Vol.124 (2), p.99-107
Main Authors: Veronese, Augusto C., Morelli, Carlo F., Callegari, Rosella, Basato, Marino
Format: Article
Language:English
Subjects:
Carbon-carbon coupling
Catalysis
Catalytic reactions
Chemistry
Exact sciences and technology
General and physical chemistry
Malononitrile
Metal catalysis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
β-dicarbonyls
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Summary:Nickel acetylacetonate effectively catalyses the carbon-carbon bond formation between malononitrile and β-dicarbonyls. In these metal-catalysed reactions malononitrile behaves as an electrophile towards the intercarbonylic carbon, so exhibiting a reverse reactivity compared with that one under basic or thermal conditions. The resulting organic products are β-cyanomethylene-β-enamino dicarbonyls ( 2a–h), which are obtained in good- to fair yield. β-Iminodicarbonyl complexes of nickel(II) and copper(II), which are likely intermediates in the catalytic cycle, are synthesised by reaction of the metal β-carbonylenolate with malononitrile or of the metal acetate with the catalysis product ( 2a, d).
ISSN:1381-1169
1873-314X
DOI:10.1016/S1381-1169(97)00077-0