Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow
Abstract An electrochemical multicomponent synthesis of sulfonamides at room temperature in single‐pass flow is presented. In contrast to batch‐type electrolysis, an undivided flow cell setup with a stainless‐steel cathode and either a boron‐doped diamond (BDD) anode or a glassy carbon anode can be...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2023-12-01
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| Series: | ChemElectroChem |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/celc.202300456 |
| _version_ | 1797404653128777728 |
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| author | Johannes Schneider Dr. Stephan P. Blum Prof. Dr. Siegfried R. Waldvogel |
| author_facet | Johannes Schneider Dr. Stephan P. Blum Prof. Dr. Siegfried R. Waldvogel |
| author_sort | Johannes Schneider |
| collection | DOAJ |
| description | Abstract An electrochemical multicomponent synthesis of sulfonamides at room temperature in single‐pass flow is presented. In contrast to batch‐type electrolysis, an undivided flow cell setup with a stainless‐steel cathode and either a boron‐doped diamond (BDD) anode or a glassy carbon anode can be employed. Simply by using SO2 stock solutions, less atom‐economic sulfur dioxide surrogates can be avoided. Moreover, no additional supporting electrolytes are required due to the in‐situ generation of amidosulfinates, which also serve as intermediate for this transformation. This protocol allows sulfonamides to be synthesized directly from non‐prefunctionalized electron‐rich arenes with amines and SO2. In total, 10 examples are demonstrated with isolated yields up to 92 %. The robust scalability of this electrosynthesis with an easy downstream processing was also proven. |
| first_indexed | 2024-03-09T02:58:09Z |
| format | Article |
| id | doaj.art-888b5b21269f4af1b4df523c82d7d505 |
| institution | Directory Open Access Journal |
| issn | 2196-0216 |
| language | English |
| last_indexed | 2024-03-09T02:58:09Z |
| publishDate | 2023-12-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemElectroChem |
| spelling | doaj.art-888b5b21269f4af1b4df523c82d7d5052023-12-05T02:03:44ZengWiley-VCHChemElectroChem2196-02162023-12-011023n/an/a10.1002/celc.202300456Electrochemical Synthesis of Sulfonamides in Single‐Pass FlowJohannes Schneider0Dr. Stephan P. Blum1Prof. Dr. Siegfried R. Waldvogel2Department of Chemistry Johannes Gutenberg University Mainz Duesbergweg 10–14 55128 Mainz GermanyDepartment of Chemistry Johannes Gutenberg University Mainz Duesbergweg 10–14 55128 Mainz GermanyDepartment of Chemistry Johannes Gutenberg University Mainz Duesbergweg 10–14 55128 Mainz GermanyAbstract An electrochemical multicomponent synthesis of sulfonamides at room temperature in single‐pass flow is presented. In contrast to batch‐type electrolysis, an undivided flow cell setup with a stainless‐steel cathode and either a boron‐doped diamond (BDD) anode or a glassy carbon anode can be employed. Simply by using SO2 stock solutions, less atom‐economic sulfur dioxide surrogates can be avoided. Moreover, no additional supporting electrolytes are required due to the in‐situ generation of amidosulfinates, which also serve as intermediate for this transformation. This protocol allows sulfonamides to be synthesized directly from non‐prefunctionalized electron‐rich arenes with amines and SO2. In total, 10 examples are demonstrated with isolated yields up to 92 %. The robust scalability of this electrosynthesis with an easy downstream processing was also proven.https://doi.org/10.1002/celc.202300456electrolysismicroreactorsmulticomponent reactionsradical reactionssulfonamides |
| spellingShingle | Johannes Schneider Dr. Stephan P. Blum Prof. Dr. Siegfried R. Waldvogel Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow ChemElectroChem electrolysis microreactors multicomponent reactions radical reactions sulfonamides |
| title | Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow |
| title_full | Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow |
| title_fullStr | Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow |
| title_full_unstemmed | Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow |
| title_short | Electrochemical Synthesis of Sulfonamides in Single‐Pass Flow |
| title_sort | electrochemical synthesis of sulfonamides in single pass flow |
| topic | electrolysis microreactors multicomponent reactions radical reactions sulfonamides |
| url | https://doi.org/10.1002/celc.202300456 |
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