Abstract
Regioselective acylation of enaminones in the presence of catalysts such as nickel acetylacetonate [Ni(acac)2] and montmorillonite K-10 to give C-allylated products is reported. Nickel acetylacetonate [Ni(acac)2] complexes of β-enamino compounds react with electrophiles as phenyl isocyanate and isothiocyanate at methin carbon, in good to excellent yields.
Highlights
Introduction βEnamino compounds are important compounds due to their application as 1,3-bielectrophilic and binucleophilic synthons in synthetic organic chemistry.[1]
In continuing our previous work on the reaction of β-enamino compounds with electrophiles,[8,9] we report a facile
In order to study the reactivity of the β-enamino compounds with electrophiles, we used phenyl isocyanate or phenyl isothiocyanate as a electrophile with a series of selected acyclic β-enamino compounds (1a–f)
Summary
In order to study the reactivity of the β-enamino compounds with electrophiles, we used phenyl isocyanate or phenyl isothiocyanate as a electrophile with a series of selected acyclic β-enamino compounds (1a–f). Phenyl isocyanate and phenyl isothiocyanate permit the investigation of the competition at the nucleophilic centers, the α-carbonylic carbon and the nitrogen of the βenamino compounds in the presence of montmorillonite K-10, or nickel acetylacetonate [Ni(acac)2] as the catalyst. We have found that the metal acts as a ‘protecting group’ toward the nitrogen, so that, the nitrogen of the β-enamino compounds appears in general rather unreactive. This fact represents a distinct advantage in terms of chemoselectivity, because, electrophiles attack almost exclusively the methine carbon instead of the nitrogen (Scheme 1)
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