posted on 2021-12-08, 17:03authored byStanislav
A. Paveliev, Oleg O. Segida, Andrey Dvoretskiy, Mark M. Dzyunov, Uliana V. Fedorova, Alexander O. Terent’ev
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%.