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

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%.

Automated summary

A novel electrochemical process was developed for the difunctionalization of vinyl arenes with N-hydroxyphthalimide, resulting in vicinal dioxyphthalimides. The reaction involves the anodic generation of stabilized phthalimide-N-oxyl radical, which adds to the carbon-carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical to afford a wide range of dioxyphthalimides with yields up to 81%.