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

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). © The Royal Society of Chemistry 2009.