Regioselective epoxide ring opening mediated by iron oxide-pillared clay

Abstract

Iron oxide pillared clays (FeOx-pillared clays) such as FeOx-pillared hectorite and FeOx-pillared bentonite were synthesized by the intercalation of iron (III) chloride into clay interlayers and calcined at 300°C. The synthesized catalysts were utilized for styrene oxide ring opening by methanol, comparing with raw clays and Fe2O3. FeOx-pillared bentonite efficiently catalyzed the ring-opening of epoxides to produce β-alkoxyalcohols in excellent yields under extremely mild reaction conditions. The quantitative yield of 2-methoxy-2-phenylethanol was obtained using 30wt% FeOx-pillared bentonite to styrene oxide at 70°C for 10min. The optimized condition was applied to the ring opening of different epoxides such as 1-dodecene oxide, cyclohexene oxide, butyl glycidyl ether, tert-butyl glycidyl ether and α-pinene oxide to furnish the desired products in moderate to excellent yields.