Electrifying Phthalimide-<i>N</i>-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with <i>N</i>-Hydroxyphthalimide
Stanislav A. Paveliev, Oleg O. Segida, Andrey Dvoretskiy, Mark M. Dzyunov, Uliana V. Fedorova, Alexander O. Terent’ev
Abstract
An electrochemical process of free-radical difunctionalization of vinyl arenes with N-hydroxyphthalimide resulting in vicinal dioxyphthalimides was discovered. The reaction proceeds with the use of pyridinium perchlorate and pyridine as a supporting electrolyte and a base, respectively. The present approach involves the anodic generation of stabilized phthalimide-N-oxyl (PINO) radical, which adds to the carbon–carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical. A wide range of dioxyphthalimides were obtained in yields up to 81%.
Topics & Concepts
PhthalimideChemistryPyridiniumElectrochemistryPyridinePolymer chemistryPerchlorateRadicalPhotochemistryOrganic chemistryElectrodePhysical chemistryIonRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods