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A Versatile and Fast Photocatalyzed Deoxygenation of Organic N-oxides with a Rhenium Complex in the Presence of H2O

Year: 2024

Type: preprint

Abstract: The oxidation of N-heterocycles is key to their functionalization since it enhances their reactivity in the ortho position. How-ever, an efficient post-reduction is often required to access the targeted compound. Here, a rhenium-based photocatalyst enables the versatile and fast deoxygenation of N-heterocyclic and alkyl N-oxides, avoiding sacrificial oxophilic reagents. The strong influence of the reaction conditions (solvent, H2O as additive, irradiation set-up) is demonstrated. The system shows a high functional group tolerance towards other reducible functions (free alcohol, carboxylic acid, ester, nitrile, halo-gen,…) and light-sensitive N-heterocycles.

Source: ChemRxiv

DOI: 10.26434/chemrxiv-2024-blth5-v2

Authors: Nicolas Joly, Marianne Kjellberg, Alexis Bouchet, Emmanuel Nicolas, Thibault Cantat, Lucile Anthore-Dalion

Institutions: Centre National de la Recherche Scientifique, Commissariat à l'Énergie Atomique et aux Énergies Alternatives, Université Paris-Saclay, CEA Paris-Saclay - Etablissement de Saclay, CEA Paris-Saclay

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, H2020 European Research Council

Awards: Renewable Hydride Donors and Their Utilization in Catalytic Reduction and Deoxygenation Reactions, Deoxygenation of N–O and S–O Bonds – A Photo- and Electrochemical Approach, Transfer Carboaminations of Alkenes with O-Acylated Hydroxylamines

OpenAlex ID: W4400568131

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Cited by: 1

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