Subscribe to RSS
DOI: 10.1055/a-2649-0086
Water-Mediated Rhenium-Catalyzed Photodeoxygenation of Polyfunctional Organic N-oxides
Supported by: Centre National de la Recherche Scientifique
Supported by: Commissariat à l'Énergie Atomique et aux Énergies Alternatives
Supported by: Agence Nationale de la Recherche ANR-21-CE07-0060,ANR-22-CE07-0028
Supported by: Labex Charmmmat
Supported by: ADEME
Supported by: H2020 European Research Council 818260
The oxidation of N-heterocycles is key to their functionalization since it enhances their reactivity in the ortho position. However, an efficient post-reduction is often required to access the targeted compound. Here, an air-stable rhenium(I)-based photocatalyst enables the fast deoxygenation of N-heterocyclic and alkyl N-oxides, avoiding sacrificial oxophilic reagents. We demonstrate that adding H2O dramatically accelerates the reaction rate. The system tolerates air contamination, is scalable, and shows a high functional group tolerance towards other reducible functions (free alcohol, carboxylic acid, ester, nitrile, halogen,…) and light-sensitive N-heterocycles.
Publication History
Received: 02 June 2025
Accepted after revision: 03 July 2025
Accepted Manuscript online:
03 July 2025
© . Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany