Electrifying Phthalimide--Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with -Hydroxyphthalimide.

An electrochemical process of free-radical difunctionalization of vinyl arenes with -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--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%.