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Dendritic Fluoroalcohols Catalyzed Alkene Epoxidation with H2O2
Dendritic Fluoroalcohols as Catalysts for Alkene Epoxidation with Hydrogen Peroxide.
Angew. Chem. Int. Ed. 2013;
15 March 2013 (online)
Hyperbranched polyglycerol immobilized flluoroalcohols (catalyst A and B) were prepared and applied to the epoxidation of alkenes. Thus, the reaction of alkenes 1 and aqueous hydrogen peroxide with 20 mol% of the fluoroalcohol unit of the catalyst gave the corresponding epoxides 2 in up to quantitative yield.
Catalysts A and B were recovered by ultrafiltration (molecular-weight cut-off of the membrane: 5 kDa) and reused twice for the epoxidation of cyclooctene without significant loss of catalytic activity. Hexafluoro-2-propanol showed lower catalytic activity for the epoxidation of 1d under similar conditions (24 h, 2d: 14% yield).