Please use this identifier to cite or link to this item: http://doi.org/10.25358/openscience-6008
Authors: Blum, Stephan P.
Karakaya, Tarik
Schollmeyer, Dieter
Klapars, Artis
Waldvogel, Siegfried R.
Title: Metal-free electrochemical synthesis of sulfonamides directly from (hetero)arenes, SO2, and amines
Online publication date: 22-Jun-2021
Language: english
Abstract: Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non-prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron-doped diamond (BDD) electrodes and a HFIP–MeCN solvent mixture enable selective formation of the sulfonamides. In total, 36 examples are demonstrated with yields up to 85 %.
DDC: 540 Chemie
540 Chemistry and allied sciences
Institution: Johannes Gutenberg-Universität Mainz
Department: FB 09 Chemie, Pharmazie u. Geowissensch.
Place: Mainz
ROR: https://ror.org/023b0x485
DOI: http://doi.org/10.25358/openscience-6008
Version: Published version
Publication type: Zeitschriftenaufsatz
License: CC BY-NC-ND
Information on rights of use: https://creativecommons.org/licenses/by-nc-nd/4.0/
Journal: Angewandte Chemie
60
10
Pages or article number: 5056
5062
Publisher: Wiley-VCH
Publisher place: Weinheim
Issue date: 2021
ISSN: 1521-3773
Publisher URL: https://doi.org/10.1002/anie.202016164
Publisher DOI: 10.1002/anie.202016164
Appears in collections:JGU-Publikationen

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