ArticleNature communications2023
An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Photochemical Cascade Nitrile Activation via a Carbene-Nitrene Relay.Angewandte Chemie (International ed. in English) · 2026Article
- Photo-induced selective N-N bond construction via harnessing nitrene release and transfer.Nature communications · 2026Article
- High-valent sulfur fluorides as reactivity switches for PFAS-free benzene-azepine skeletal editing.Chemical science · 2026Article
- Photocatalytic Synthesis of Unprotected Sulfonimidamides and Their Application in Photochemical Nitrene Transfer Reactions.Angewandte Chemie (International ed. in English) · 2025Article
- Is Phenylnitrene a Missing Link in the Formation of Polycyclic Aromatic Nitrogen Heterocycles?Angewandte Chemie (International ed. in English) · 2025Article
- Allylic Hydrogen Acidity of 1-Butene Derivatives Coordinated to Transition Metals─A Mechanistic Insight Including Carbonyl-Olefin Metathesis.Inorganic chemistry · 2025Article
- Article
- Review
- DFT Mechanistic Investigation into Ni(II)-Catalyzed Hydroxylation of Benzene to Phenol by HInorganic chemistry · 2024Article
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Authors and funding
7 authors.
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No grant is acknowledged in the PubMed record.
Abstract
Azepinone derivatives are privileged in organic synthesis and pharmaceuticals. Synthetic approaches to these frameworks are limited to complex substrates, strong bases, high power UV light or noble metal catalysis. We herein report a mild synthesis of azepinone derivatives by a photochemical generation of 2-aryloxyaryl nitrene, [2 + 1] annulation, ring expansion/water addition cascade reaction without using any metal catalyst. Among the different nitrene precursors tested, 2-aryloxyaryl azides performed best under blue light irradiation and Brønsted acid catalysis. The reaction scope is broad and the obtained products underwent divergent transformations to afford other related compounds. A computational study suggests a pathway involving a step-wise aziridine formation, followed by a ring-expansion to the seven-membered heterocycle. Finally, water is added in a regio-selective manner, this is accelerated by the added TsOH.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.