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Regioselective Ring Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex.

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A new Fe(III)-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, is reported to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol% of catalyst and 80 °C).… Click to show full abstract

A new Fe(III)-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, is reported to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol% of catalyst and 80 °C). The reaction proceeds with high activity (initial turnover frequency of 1680 h-1 for ethanol) and selectivity (>95%) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84-96% of non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule, such as glycidol, to high value-added products using an Earth-crust abundant metal-based catalyst.

Keywords: ring opening; glyceryl ethers; opening glycidol; triflate complex; monoalkyl glyceryl

Journal Title: ChemSusChem
Year Published: 2019

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