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

✍ Scribed by Augusto C. Veronese; Carlo F. Morelli; Rosella Callegari; Marino Basato

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 818 KB
• Volume: 124
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(97)00077-0

✦ Synopsis

Nickel acetylacetonate effectively catalyses the carbon-carbon bond formation between malononitrile and P-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 /3-cyanomethylene-fi-enamino dicarbonyls (2a-h), which are obtained in good-to fair yield. P-Iminodicarbonyl complexes of nickel(I1) and copper(U), which are likely intermediates in the catalytic cycle, are synthesised by reaction of the metal @trbonylenolate with malononitrile or of the metal acetate with the catalysis product (2a, d).