Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines
- Publication type:
- Journal article
- Metadata:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>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 SO<jats:sub>2</jats:sub> 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 %.</jats:p>
- Autoren
- Stephan P Blum
- Tarik Karakaya
- Dieter Schollmeyer
- Artis Klapars
- Siegfried R Waldvogel
- DOI
- 10.1002/anie.202016164
- eISSN
- 1521-3773
- ISSN
- 1433-7851
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Angewandte Chemie International Edition
- Sprache
- en
- Online publication date
- 2021
- Paginierung
- 5056 - 5062
- Datum der Veröffentlichung
- 2021
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/anie.202016164
- Datum der Datenerfassung
- 2023
- Titel
- Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO<sub>2</sub>, and Amines
- Ausgabe der Zeitschrift
- 60
Data source: Crossref
- Other metadata sources:
-
- Author's licence
- CC-BY-NC-ND
- Autoren
- Stephan P Blum
- Tarik Karakaya
- Dieter Schollmeyer
- Artis Klapars
- Siegfried R Waldvogel
- Hosting institution
- Universitätsbibliothek Mainz
- Sammlungen
- JGU-Publikationen
- Resource version
- Published version
- DOI
- 10.1002/anie.202016164
- File(s) embargoed
- false
- Open access
- true
- ISSN
- 1521-3773
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Angewandte Chemie
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Open access status
- Open Access
- Paginierung
- 5056 - 5062
- Datum der Veröffentlichung
- 2021
- Public URL
- https://openscience.ub.uni-mainz.de/handle/20.500.12030/6017
- Herausgeber
- Wiley-VCH
- Herausgeber URL
- https://doi.org/10.1002/anie.202016164
- Datum der Datenerfassung
- 2021
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2021
- Zugang
- Public
- Titel
- Metal-free electrochemical synthesis of sulfonamides directly from (hetero)arenes, SO2, and amines
- Ausgabe der Zeitschrift
- 60
Files
blum_stephan_p.-metal-free_ele-20210607143716399.pdf
Data source: OPENSCIENCE.UB