s-Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

2021/11/09 by Géraldine Masson, Jiyuan Lyu, Tuan Le +3
Chemistry · #Oxidative Organic Chemistry Reactions #Radical Photochemical Reactions #Sulfur-Based Synthesis Techniques

paper · doi:10.1055/a-1691-0449

openalex publication_date 2021/11/09 · openalex created_date 2021/11/22 · openalex updated_date 2026/07/22

Abstract

Abstract Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.

Citations

• Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis
• On the Oxidation of Hydroxylamines with o-Iodoxybenzoic Acid (IBX)
• Generation and Detection of Reactive Oxygen Species in Photocatalysis

Related

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• The Reaction of Nitrones with Cyclopropanes: A Convenient Preparation of Tetrahydro-1,2-oxazines
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• Divergent [3+2] Photocycloadditions of Nitrones to Isoxazolines and Oxa-Aza-Bicycloheptanes: Controlling Entry and Exit from Flatland
• One-Step Photoreduction of Nitroarenes to Nitrosoarenes