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

0582013 - ÚFCH JH 2025 RIV US eng J - Journal Article
Salvadori, Karolína - Churý, M. - Budka, J. - Harvalík, J. - Matějka, P. - Šimková, Ludmila - Lhoták, P.
Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides.
Journal of Organic Chemistry. Roč. 89, č. 3 (2024), s. 1425-1437. ISSN 0022-3263. E-ISSN 1520-6904
Institutional support: RVO:61388955
Keywords : electrochemistry * electrolysis * sulfonamides
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impact factor: 3.6, year: 2022
Method of publishing: Open access
https://pubs.acs.org/doi/10.1021/acs.joc.3c01932

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 (only0.9 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 complex molecule. Thus, the method is interesting for use in the field of multifunctional molecules such as calix[n]arenes.
Permanent Link: https://hdl.handle.net/11104/0350143