ArticleChemistry (Weinheim an der Bergstrasse, Germany)2017
Sulfonylative and Azidosulfonylative Cyclizations by Visible-Light-Photosensitization of Sulfonyl Azides in THF.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Gold-Catalyzed Cyclizations of 4-Alkyl-2-yn-1-yl (Oxy)cyclohexa-2,5-dien-1-ones (Organic letters · 2026Article
- Photocatalytic Nitrene Radical Anion Generation from Sulfonyl Azides for Intermolecular Aziridination of Unactivated Alkenes.The Journal of organic chemistry · 2025Article
- Regioselective Radical Cascade Cyclizations of Alkyne-Tethered Cyclohexadienones with Chalcogenides under Visible-Light Catalysis.ACS omega · 2023Article
- Difunctionalization of Dienes, Enynes and Related Compounds via Sequential Radical Addition and Cyclization Reactions.Molecules (Basel, Switzerland) · 2023Review
- Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides.Nature communications · 2021Article
- Iron porphyrin catalysed light driven C-H bond amination and alkene aziridination with organic azides.Chemical science · 2020Article
- Sulfonylative and Azidosulfonylative Cyclizations by Visible-Light-Photosensitization of Sulfonyl Azides in THF.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
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Authors and funding
7 authors.
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Abstract
The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiation involves the photosensitized formation of a triplet sulfonyl nitrene, which abstracts a hydrogen atom from THF to give a tetrahydrofuran-2-yl radical, which then reacts with the sulfonyl azide to generate the sulfonyl radical.
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