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RESEARCH PRODUCT
Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines
Dieter SchollmeyerArtis KlaparsSiegfried R. WaldvogelStephan P. BlumTarik Karakayasubject
chemistry.chemical_classificationGreen chemistryradical reactions010405 organic chemistrySupporting electrolytegreen chemistryoxidationCommunicationGeneral Chemistry010402 general chemistryElectrochemistry01 natural sciencesCombinatorial chemistryCatalysisCommunications0104 chemical sciencesSulfonamideSolventchemistryNucleophileElectrochemistry | Hot PaperelectrochemistrysulfonamidesElectrodeReactivity (chemistry)description
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 %.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-02-01 | Angewandte Chemie (International Ed. in English) |