Silica Nanoparticles Functionalized with an Ionic Liquid: A Green and Efficient Heterogeneous Catalyst for a Cascade Reaction

A new strategy for a catalytic C-C bond forming cascade reaction comprising acetal hydrolysis and Knoevenagel condensation is presented here. The heterogeneous nanocatalyst is prepared by immobilizing an ionic liquid on the surface of highly monodisperse silica nanoparticles. This work is the first example of showing that there is no need to use bifunctional acid-base catalysts for a cascade reaction including the hydrolysis of benzaldehyde dimethyl acetal to benzaldehyde and the subsequent Knoevenagel condensation of the resulting benzaldehyde with malononitrile. It is shown here that these reactions can proceed smoothly with a mono-functional heterogeneous catalyst that contains a neutral ionic liquid. It has been proposed that such a neutral ionic liquid can "switch on" to an acidic catalyst in conjunction with water. The selected ionic liquid has potentially biodegradability characteristics, which is an important issue to achieve a sustainable catalyst. The simple procedure for preparing both the ionic liquid and the monodisperse silica nanoparticles provides opportunities for a large-scale synthesis of the catalyst. This work introduces a breakthrough in the design and synthesis of heterogeneous catalysts for acid/base catalyzed cascade organic reactions.