Oligo(ethylene glycol) Length Effect of Water-Soluble Ru-Based Olefin Metathesis Catalysts on Reactivity and Removability

A study of reaction kinetics and removal efficiency of a family of ruthenium (Ru)-based olefin metathesis catalysts containing ethylene-glycol-oligomer-tethered N-heterocyclic carbene (NHC) ligands has been carried out, with a focus on variation of ethylene glycol oligomer length. The length of ethylene glycol oligomer was precisely defined by sequential addition of repeating units. Due to the dual solubility of ethylene glycol oligomer, the produced catalyst was highly soluble in both aqueous and organic solvents (dichloromethane). In aqueous solution, the polarity increase with longer ethylene glycol oligomers enhanced the reactivity in homogeneous solution. The length of ethylene glycol oligomer did not significantly affect olefin metathesis rate in organic solution. Yet the removal efficiency of catalyst strongly relies on the length of ethylene glycol oligomer. A longer ethylene glycol oligomer demonstrated better catalyst removal efficiency. The tested catalyst removal method was aqueous extraction from organic solution using its higher water solubility property compared to its lower organic solvent (dichloromethane) solubility property. The results obtained from the aqueous extraction catalyst removal method demonstrated similar and/or better removal rates compared to previously reported host-guest catalyst removal methods.