Palladium-catalyzed epoxidation of olefins using electrophiles as oxidizing agents

Abstract

A palladium-catalyzed olefin epoxidation reaction was developed using electrophilic reagents as oxidants. The modular synthesis of various alkyl alcohols, alkyl esters, and alkyl halides was achieved in good to excellent yields. These products can be used to synthesize potential drug ibuprofen derivatives. A preliminary mechanistic study shows that SN2 attack by the nucleophilic reagents in the system creates the final C–O bond and an SN1 reaction of halide ions creates a C–X bond.