Researchers of the ZIOC carried out an electrochemical difunctionalization of alkenes with the use of N-oxyl radicals

Selective radical difunctionalization of alkenes is one of the most dynamically developing and attractive areas of research in modern organic synthesis. An electrochemical process of free radical difunctionalization of alkenes under the action of N-hydroxyphthalimide was discovered at the Laboratory for the Study of Homolytic Reactions of the Zelinsky Institute.

The implementation of reactions involving N-oxyl radicals under electrochemical conditions is problematic due to their tendency to decomposition and cathodic reduction. Only a few examples of addition reactions of N-oxyl radicals generated by electric current are known. It was found that imide-N-oxyl radicals generated at the N-hydroxyphthalimide anode add twice to the C=C multiple bond of various alkenes to form vicinal dihydroxyphthalimides. It should be noted that electric current allows the reaction to be carried out without the use of traditional chemical oxidizing agents.

Source:

Stanislav A. Paveliev, Oleg O. Segida, Anrey Dvoretskiy, Mark M. Dzyunov, Uliana V. Fedorova, Alexander O. Terent’ev Electrifying Phthalimide-N-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with N-Hydroxyphthalimide. J. Org. Chem., 2021, 86, 24, 18107-18116. DOI: 10.1021/acs.joc.1c02367.