Organic–inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts as recyclable organocatalysts for Knoevenagel condensations

Abstract

Organic–inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts prepared from monosilylated and disilylated monomers by sol–gel methodologies are active and reusable organocatalysts for the Knoevenagel condensation of aromatic aldehydes with malononitrile and ethyl cyanoacetate under solvent-free conditions. Our immobilized systems present higher activities than related homogeneous bis-imidazolium salts, showing the cooperative effect of the matrix surface and the additional advantage of easy recycling. The best performances were obtained with the material derived from polycondensation of a disilylated dihydroimidazolium salt in the absence of tetraethoxysilane (TEOS).