ArticleThe Journal of organic chemistry2024
Organic Dye-Sensitized Nitrene Generation: Intermolecular Aziridination of Unactivated Alkenes.
Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Modular diastereoselective synthesis of hindered cyclobutane amino nitriles through triplet nitrene-mediated ring expansion.Nature chemistry · 2026Article
- Ultrafast Photochemical Reaction Dynamics of 3-Phenyl-1,4,2-dioxazol-5-one Revealed by Femtosecond Time-Resolved Infrared Spectroscopy.International journal of molecular sciences · 2026Article
- Harnessing Cooperative Energy Transfer and Hydrogen Atom Transfer for Direct Nitrogenations of Non-Activated Alkanes.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes.The Journal of organic chemistry · 2025Article
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Authors and funding
6 authors.
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Abstract
Aziridines are important structural motifs and intermediates, and several synthetic strategies for the direct aziridination of alkenes have been introduced. However, many of these strategies require an excess of activated alkene, suffer from competing side-reactions, have limited functional group tolerance, or involve precious transition metal-based catalysts. Herein, we demonstrate the direct aziridination of alkenes by combining sulfonyl azides as a triplet nitrene source with a catalytic amount of an organic dye functioning as photosensitizer. We show how the nature of the sulfonyl azide, in combination with the triplet-excited state energy of the photosensitizer, affects the aziridination yield and provide a mechanistic rationale to account for the observed dependence of the reaction yield on the nature of the organic dye and sulfonyl azide reagents. The optimized reaction conditions enable the aziridination of structurally diverse and complex alkenes, carrying various functional groups, with the alkene as the limiting reagent.
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Registered trials
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