Regioselective epoxide ring opening mediated by iron oxide-pillared clay

•FeOx-pillared bentonite has been successfully synthesized.•The structure of synthesized pillared clay was well-characterized.•The prepared clay was used as a catalyst in ring-opening of epoxide.•The reaction can proceed under mild conditions with high yield and good selectivity.•Several examples are displayed to reveal the scope of the reaction.

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 30 wt% FeOx-pillared bentonite to styrene oxide at 70 °C for 10 min. 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.

Graphical abstractFeOx-pillared bentonite has been successfully developed for the ring opening of styrene oxide under mild reaction conditions furnishing quantitative yield of 2-methoxy-2-phenylethanol.Figure optionsDownload full-size imageDownload high-quality image (73 K)Download as PowerPoint slide