Rearrangement of Epoxides by Iron complexes

Abstract

Epoxides are one of the most useful and versatile intermedieates in organic synthesis due to their high reactivity and easy availability through a wide variety of methods, and also undergo numerous modes of subsequent transformation. This work focused on the development of a new synthetic methodology for the preparation of carbonyl compound. With the use of iron(III) acetylacetonate as a reagent, the rearrangement of aryl-substituted epoxides with hydride migration was proceeded to only ketone product via Lewis acid promoted C-O bond cleavage and cationic species. This method was carried out in short period of time under mild conditions using commercial solvents, such as hexane and EtOAc. The optimized conditions were accomplishedly applied to the rearrangement of a variety of different aryl-substituted epoxides to furnish the desired products in moderate to excellent yields.