Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides.

ABSTRACT: A new method for selective cleavage of sulfonimides into sulfonamides in high yields using a simple electrochemical approach is shown. As revealed by the electrochemical study, the aromatic sulfonimides can be selectively cleaved by electrolysis of the starting compound at a given potential (only -0.9 V vs SCE for the nosyl group). The high chemoselectivity was confirmed by preparative electrolysis, and the results were supported with DFT calculations of a set of substances bearing different sulfonimide functions. Moreover, various experimental setups together with other attempts to simplify the procedure were tested. Finally, the removal of the p-nosyl group from the corresponding sulfonimides proceeds smoothly regardless of the number of nosyl groups and the overall shape of the c

SUBMITTER: Salvadori K 

PROVIDER: S-EPMC10845148 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature