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

Karolína Salvadori, Michal Churý, Jan Budka, Jakub Harvalík, Pavel Matějka, Ludmila Šimková, Pavel Lhoták

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Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

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7 authors.

Karolína SalvadoriJ. Heyrovský Institute of Physical Chemistry of Czech Academy of Sciences v.v.i., Dolejškova 2155/3, 182 23 Prague 8, Czech Republic.

Michal ChurýDepartment of Organic Chemistry, UCTP, Technická 5, 166 28 Prague 6, Czech Republic.

Jan BudkaDepartment of Organic Chemistry, UCTP, Technická 5, 166 28 Prague 6, Czech Republic.

Jakub HarvalíkDepartment of Physical Chemistry, University of Chemistry and Technology, Prague (UCTP), Technická 5, 166 28 Prague 6, Czech Republic.

Pavel MatějkaDepartment of Physical Chemistry, University of Chemistry and Technology, Prague (UCTP), Technická 5, 166 28 Prague 6, Czech Republic.

Ludmila ŠimkováJ. Heyrovský Institute of Physical Chemistry of Czech Academy of Sciences v.v.i., Dolejškova 2155/3, 182 23 Prague 8, Czech Republic.

Pavel LhotákDepartment of Organic Chemistry, UCTP, Technická 5, 166 28 Prague 6, Czech Republic.ORCID 0000-0003-3617-6596

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

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

Identifiers

PMID38198698

DOI10.1021/acs.joc.3c01932

PMCPMC10845148

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