Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines
At a Glance
Section titled “At a Glance”| Metadata | Details |
|---|---|
| Publication Date | 2020-12-29 |
| Journal | Angewandte Chemie International Edition |
| Authors | Stephan P. Blum, Tarik Karakaya, Dieter Schollmeyer, Artis Klapars, Siegfried R. Waldvogel |
| Institutions | Merck & Co., Inc., Rahway, NJ, USA (United States), Johannes Gutenberg University Mainz |
| Citations | 90 |
Abstract
Section titled “Abstract”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 SO 2 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 %.
Tech Support
Section titled “Tech Support”Original Source
Section titled “Original Source”References
Section titled “References”- 2019 - Critically Important Antimicrobials for Human Medicine