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Synthesis
DOI: 10.1055/a-2649-0086
DOI: 10.1055/a-2649-0086
Paper
Published as part of the Special Topic Dedicated to Prof. Paul Knochel
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
Funding Information We thank the CEA, CNRS, ERC (Consolidator Grant no. 818260), and ANR (PRC grant no. ANR-22-CE07-0028, JCJC grant no. ANR-21-CE07-0060) for funding. M.K. was supported by a Master’s fellowship from the LABEX Charmmmat followed by a PhD fellowship from ADEME/CEA.
Dedication
Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.
Abstract
The oxidation of N-heterocycles is key to their functionalization as 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 toward other reducible functions (free alcohol, carboxylic acid, ester, nitrile, halogen, etc.) and light-sensitive N-heterocycles.
Publication History
Received: 02 June 2025
Accepted after revision: 03 July 2025
Accepted Manuscript online:
03 July 2025
Article published online:
07 August 2025
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