Researchers of the Zelinsky Institute have proposed a new electrochemical method for the sulfonylation of alkenes

Oxidative coupling allows to create a variety of chemical bonds without the introduction of functional groups. This is ensured by the presence in the reaction mixture, along with the reagents, of an oxidizing agent in a stoichiometric amount. Electric current is one of the promising oxidizing agents in such transformations, since it makes it possible to avoid adding stoichiometric amounts of an oxidizing agent. By changing various electrosynthesis parameters, one can finely tune the reactivity of the starting compounds. However, a significant simplification of the electrolysis parameters in such reactions often leads to low selectivity, and therefore the search for a compromise between the simplicity and efficiency of electrosynthesis sometimes becomes an important aspect in these processes.

Oxidative electrochemical C–S coupling can become an alternative for the synthesis of various organosulfur compounds. In most of these processes, thiols are used as S-partners, which can be converted into less reactive disulfides. For a long time, disulfides, relatively inert in such reactions, were of little interest as S-partners.

Scientists from the Laboratory for the Study of Homolytic Reactions of the ZIOC have developed an electrochemical method for the sulfonylation of alkenes using disulfides, which are relatively inert under electrochemical conditions, as a sulfonylating agent. The reaction takes place in a galvanostatic mode using a structurally simple undivided electrochemical cell with the formation of exclusively trans-vinyl sulfones. During the study, it was found that the presence of iodine electrolyte and water plays an important role in the formation of end products.

Source:

Olga M. Mulina, Mikhail M. Doronin, Liang-Nian He, Alexander O. Terent’ev Disulfides as versatile starting reagents: effective sulfonylation of alkenes with disulfides under electrochemical conditions // Org. Chem. Front., 2023, accepted manuscript. DOI: 10.1039/d3qo00589e.