Regioselective Ring‐Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]‐FeIII Triflate Complex. Issue 15 (17th July 2019)

• Record Type: Journal Article
• Authors: Monica, Francesco Della; Ricciardi, Maria; Proto, Antonio; Cucciniello, Raffaele; Capacchione, Carmine
• Is Part Of: ChemSusChem. Volume 12:Issue 15(2019)
• Page Start: 3448
• Page End: 3452
• Publication Date: 2019-07-17
• Subjects: glyceryl ethers -- glycidol -- homogeneous catalysis -- iron -- ring-opening; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201901329
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: A Fe III ‐triflate complex, bearing a bis‐thioether‐di‐phenolate [OSSO]‐type ligand, was discovered to promote the ring‐opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h −1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non‐symmetric regioisomer). This synthetic approach allows the conversion of a glycerol‐derived platform molecule (i.e., glycidol) to high‐value‐added products by using an Earth‐crust abundant metal‐based catalyst. Abstract : The use of an Earth‐crust abundant metal‐based catalyst is proposed for the regioselective production of monoalkyl glyceryl ethers through ring‐opening of glycidol with alcohols under mild reaction conditions.