Effect of immobilization on catalytic characteristics of saturated Pd-N-heterocyclic carbenes in Mizoroki–Heck reactions

A saturated Pd-N-heterocyclic complex was immobilized on an amorphous silica. The complex itself is of very high thermal stability. However, TEM observations, hot filtration, reusability, and poisoning tests all revealed that the complex acted only as a precatalyst to highly active Pd species in Mizoroki–Heck reactions when immobilized. The complex appears more stable when used under homogeneous reaction conditions. The immobilized complex afforded high turnover numbers, 104–105. The higher turnover frequencies were realized at the lower Pd concentrations, which is a characteristic property of ligand-free Pd catalyzed reactions.