Direct Assembly of Polysubstituted Furans via C(sp3)−H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon

Abstract An unusual I2‐mediated triple C(sp3)−H functionalization reaction between aryl methyl ketones and dimethyl sulfoxide to form polysubstituted furans has been developed. In this transformation, dimethyl sulfoxide functions as a dual synthon via C(sp3)−H functionalization with formation of two C−C bonds, one C−O bond, and one C−S bond in a one‐step process. Iodine is crucial as promoter of the reaction, by which a number of ketones could be converted easily into 2,4,5‐trisubstituted furans. This provides an extremely simple and expeditious approach to high‐value‐added, biologically significant O‐heterocycles. Based on preliminary experiments, a plausible mechanism is proposed. magnified image