Binol derivative ligand immobilized onto silica: Alkyl-cyanohydrin synthesis via sequential hydroformylation/heterogeneous cyanosilylation reactions

•Immobilization and characterization of BINOL metal complexes onto aminated silica.•Efficient sequential catalytic hydroformylation/cyanosilylation process.•Sequential catalysis allows direct access to high value hydroxyacids, from olefins.

A new 6,6′-dicarboxyl-BINOL type ligand, was synthesized and anchored onto a aminated silica. Full characterization of the solids was carried out by means of thermogravimetry/differential scanning calorimetry, N2 adsorption, infra red and UV–vis diffuse reflectance spectroscopy techniques. Comparative studies between homogeneous versus heterogeneous catalytic cyanosilylation reactions of aldehydes were carried out, and similar activities were obtained. Furthermore, an efficient sequential process to promote the hydroformylation of 1-octene into nonanal followed by in situ cyanosilylation of the aldehyde, catalyzed by titanium immobilized BINOL derivative, is described. Reutilization studies of cyanosilylation catalyst revealed that the new titanium immobilized catalyst could be reused with 25% loss of activity after 3 reuses.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (119 K)Download as PowerPoint slide