Visible-Light-Enabled Oxidative Alkylation of Unactivated Alkenes with Dimethyl Sulfoxide through Concomitant 1,2-Aryl Migration.

Metal-free oxidative radical 1,2-alkylarylation of unactivated alkenes with the α-C(sp3)-H bond of dimethyl sulfoxide has been developed. This study realizes a new, conceptually novel technology for convenient construction of a variety of α-aryl-γ-methylsulfinyl ketones in good-to-excellent yields with the synergistic interactions of visible light irradiation, organic fluorophores 4CzIPN, and hypervalent iodine(III) reagent under transition-metal free conditions. A remarkable kinetic isotope effect was observed, which helped provide insight into the reaction's mechanistic course.