Iodobenzene Dicarboxylates as Transferrable Oxygen Sources: Synthesis of α-Oxygenated Ketones from Terminal Aryl Alkynes

Abstract

A facile and efficient method for preparation of α-oxygenated ketones has been developed via the reaction of terminal aryl alkynes with various iodobenzene dicarboxylates. When bis(trifluoroacetoxy)iodobenzene (PIFA) was used, α-hydroxy ketones were obtained in high to excellent yields. The hypervalent iodine(III) reagents can function as an electrophile, transferrable O-nucleophile, and an excellent leaving group. The protocol represents a direct, atom-efficient and metal-free conversion of alkynes into α-oxygenated ketones under mild conditions.