ArticleNature chemistry2024
Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 86 citations in OpenAlex.
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- Oxidative Arene Ring-Opening of Benzylic Alcohols.JACS Au · 2026Article
- Reactivity of Nitroarenes toward Alkyl Radicals Enables Direct C-H Alkylation.Journal of the American Chemical Society · 2026Article
- Photo-induced terminal alkyne insertion into arene ring to synthesize boron-doped polycycles.Chemical science · 2026Article
- Photocatalytic Denitrative Homo- and Cross-Coupling of Nitroalkanes toward the Synthesis of Alkenes.Journal of the American Chemical Society · 2026Article
- Photo-Stitching of Nitroalkanes via Cross-Denitrative Olefination.Journal of the American Chemical Society · 2026Article
- Lactam Framework Editing via Formal Methylene Deletion.Journal of the American Chemical Society · 2026Article
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Asymmetric hydrogenation of 3Chemical science · 2026Article
- Photochemical C4-Selective C-H Amination of Quinolines viaOrganic letters · 2026Article
- Skeletal editing of tetrahydrofurans to pyrrolidines through O-to-N single atom swap.Nature communications · 2026Article
- High-valent sulfur fluorides as reactivity switches for PFAS-free benzene-azepine skeletal editing.Chemical science · 2026Article
- Skeletal Editing of Alkenes with Nitroarenes via Photoinduced Rearrangement of N─O═C Dipoles Forms Lactams and Amides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Cooperative Brønsted Acid and Photo-Promoted Stereoselective Synthesis of Substituted Piperidones.Angewandte Chemie (International ed. in English) · 2025Article
- Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines.Nature communications · 2025Article
- Photocatalytic Synthesis of Unprotected Sulfonimidamides and Their Application in Photochemical Nitrene Transfer Reactions.Angewandte Chemie (International ed. in English) · 2025Article
- Visible light promotes PACS catalysis · 2025Article
- Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition.Nature communications · 2025Article
- Hydrogen Atom Transfer-Based C(spThe Journal of organic chemistry · 2025Article
Corrections and comments
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Authors and funding
10 authors at 3 institutions in 3 countries.
Funding
Abstract
The synthesis of functionalized nitrogen heterocycles is integral to discovering, manufacturing and evolving high-value materials. The availability of effective strategies for heterocycle synthesis often biases the frequency of specific ring systems over others in the core structures of bioactive leads. For example, while the six- and five-membered piperidine and pyrrolidine are widespread in medicinal chemistry libraries, the seven-membered azepane is essentially absent and this leaves open a substantial area of three-dimensional chemical space. Here we report a strategy to prepare complex azepanes from simple nitroarenes by photochemical dearomative ring expansion centred on the conversion of the nitro group into a singlet nitrene. This process is mediated by blue light, occurs at room temperature and transforms the six-membered benzenoid framework into a seven-membered ring system. A following hydrogenolysis provides the azepanes in just two steps. We have demonstrated the utility of the strategy with the synthesis of several azepane analogues of piperidine drugs.
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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.