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Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides.
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SYSNO ASEP 0582013 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides. Tvůrce(i) Salvadori, Karolína (UFCH-W)
Churý, M. (CZ)
Budka, J. (CZ)
Harvalík, J. (CZ)
Matějka, P. (CZ)
Šimková, Ludmila (UFCH-W) RID, ORCID
Lhoták, P. (CZ)Zdroj.dok. Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 89, č. 3 (2024), s. 1425-1437Poč.str. 13 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova electrochemistry ; electrolysis ; sulfonamides Obor OECD Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis) Způsob publikování Open access Institucionální podpora UFCH-W - RVO:61388955 UT WOS 38198698 EID SCOPUS 85182557502 DOI 10.1021/acs.joc.3c01932 Anotace 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. Pracoviště Ústav fyzikální chemie J.Heyrovského Kontakt Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Rok sběru 2025 Elektronická adresa https://pubs.acs.org/doi/10.1021/acs.joc.3c01932
Počet záznamů: 1