Base-Mediated C4-Selective C−H-Sulfonylation of Pyridine**
- The direct regioselective C−H-functionalization of simple, unfunctionalized pyridines is considered a long-standing challenge in heterocyclic chemistry. Herein, we report a novel one-pot protocol for the C4-selective sulfonylation of pyridines via triflic anhydride (Tf2O) activation, base-mediated addition of a sulfinic acid salt, and subsequent elimination/re-aromatization. Contrary to previous approaches employing tailored blocking groups, positional selectivity can be controlled by using N-methylpiperidine as simple, readily available external base. This method offers a highly modular and streamlined access to C4-sulfonylated pyridines.
Author: | Marius Friedrich, Georg ManolikakesORCiD |
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URN: | urn:nbn:de:hbz:386-kluedo-80664 |
DOI: | https://doi.org/10.1002/ejoc.202200915 |
ISSN: | 1099-0690 |
Parent Title (English): | European Journal of Organic Chemistry |
Publisher: | Wiley |
Document Type: | Article |
Language of publication: | English |
Date of Publication (online): | 2024/04/17 |
Year of first Publication: | 2022 |
Publishing Institution: | Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau |
Date of the Publication (Server): | 2024/04/17 |
Issue: | 2022/34 |
Page Number: | 4 |
Source: | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202200915 |
Faculties / Organisational entities: | Kaiserslautern - Fachbereich Chemie |
DDC-Cassification: | 5 Naturwissenschaften und Mathematik / 540 Chemie |
Collections: | Open-Access-Publikationsfonds |
Licence (German): | Zweitveröffentlichung |