Abstract
Aqueous starfruit juice catalyzed a simple and efficient Knoevenagel condensation of aromatic aldehydes with malononitrile has been developed under visible light. Products were obtained in yields up to 98% after short reaction times and they were isolated by simple filtration in pure crystallization states. The method is green and economically viable. A plausible mechanism for photochemical Knoevenagel condensation reaction catalyzed by starfruit juice was also predicted.
Highlights
Knoevenagel condensation, first demonstrated by Emil Knoevenagel in 1894 [1], is one of the most important and widely employed methods for carbon-carbon double bond formation in synthetic chemistry [2]-[4]
We report the Knoevenagel condensation of aromatic aldehydes with malononitrile in presence of aqueous starfruit juice, a natural, green and biocatalyst system stimulated by visible light
In continuation of our research interest concerning the investigation of new natural catalyst and development of new methodologies (62 - 64, 70, 71) is reported in this paper, for the first time a highly efficient, ecofriendly and economic method for Knoevenagel condensation of aldehydes with malononitrile using aqueous starfruit juice stimulated by visible light affording 2-(substituted phenylidene) malononitrile (Scheme 1)
Summary
Knoevenagel condensation, first demonstrated by Emil Knoevenagel in 1894 [1], is one of the most important and widely employed methods for carbon-carbon double bond formation in synthetic chemistry [2]-[4]. It has been used for the preparation of a wide range of substituted electrophilic alkenes, and for the synthesis of intermediate such as coumarin derivatives which are useful in perfumes, cosmetics and bioactive compounds [5]-[8].
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