ArticleAngewandte Chemie (International ed. in English)2023
Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 78 citations in OpenAlex.
- Violet-light-induced ring expansion of 2-aryl-1,3-indandiones with chlorodiazirines toward 1,4-naphthoquinones.Chemical science · 2026Article
- Oxidative Arene Ring-Opening of Benzylic Alcohols.JACS Au · 2026Article
- Emerging Strategies forJACS Au · 2026Review
- Article
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Skeletal editing of tetrahydrofurans to pyrrolidines through O-to-N single atom swap.Nature communications · 2026Article
- Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation.Chemical science · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
- Article
- Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.JACS Au · 2025Article
- Heteroaromatic swapping in aromatic ketones.Nature communications · 2025Article
- Synthesis of Thiophenes from Pyridines Using Elemental Sulfur.Angewandte Chemie (International ed. in English) · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- The Versatility of Diazirines: Properties, Synthetic and Modern Applications.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Rh-Catalyzed Atroposelective Single-Carbon Insertion.Journal of the American Chemical Society · 2025Article
- Article
- Single-Carbon Insertion into Single C-C Bonds with Diazirines.Journal of the American Chemical Society · 2025Article
- Halogencarbene-free Ciamician-Dennstedt single-atom skeletal editing.Nature communications · 2024Article
- Direct oxygen insertion into C-C bond of styrenes with air.Nature communications · 2024Article
- Asymmetric one-carbon ring expansion of diverse N-heterocycles via copper-catalyzed diyne cyclization.Science advances · 2024Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
We demonstrate that arylchlorodiazirines serve as photo-activated halocarbene precursors for the selective one-carbon ring expansion of N-substituted pyrroles and indoles to the corresponding pyridinium and quinolinium salts. Preliminary investigations indicate that the same strategy also enables the conversion of N-substituted pyrazoles to pyrimidinium salts. The N-substituent of the substrate plays an essential role in: (1) increasing substrate scope by preventing product degradation, (2) enhancing yields by suppressing co-product inhibition, and (3) activating the azinium products towards subsequent synthetic manipulations. This latter point is illustrated by subjecting the quinolinium salts to four complementary partial reductions, which provide concise access to ring-expanded products with different degrees of increased C(sp
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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.