ArticleJournal of the American Chemical Society2021
Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 77 papers.
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Who cites it
77 citing papers in PubMed.
- Programmable Leaving Group Controlled Skeletal Editing of Pyrroles into Pyridines via Sulfenylcarbenes.ACS organic & inorganic Au · 2026Article
- Violet-light-induced ring expansion of 2-aryl-1,3-indandiones with chlorodiazirines toward 1,4-naphthoquinones.Chemical science · 2026Article
- Single-carbon insertion enables conversion of cyclopropenes into cyclobutenes: access to oxaspiro[2.3]hexenes.Chemical science · 2026Article
- Scaffold hopping of furans into 3-cyanopyridines.Nature communications · 2026Article
- Oxidative Arene Ring-Opening of Benzylic Alcohols.JACS Au · 2026Article
- Direct Access to the SimplestJACS Au · 2026Article
- Emerging Strategies forJACS Au · 2026Review
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- Bis(trifluoromethylthio)carbene as a toolbox for versatile carbene transformations.Nature communications · 2026Article
- Reprogramming RiPP scaffolds through skeletal editing unlocks chemical space.Chemical science · 2026Article
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- A difluorocarbene-triggered annulation/ring expansion cascadeChemical science · 2026Article
- Skeletal editing of tetrahydrofurans to pyrrolidines through O-to-N single atom swap.Nature communications · 2026Article
- A Rh(II) Catalyzed Atropisomer Selective Ring Expansion of 3-Aryl Indoles to 4-Aryl Quinolines.ACS catalysis · 2026Article
- Skeletal Editing via Diastereoselective Ring Expansion Enables Enantioenriched Tetrasubstituted ΔJACS Au · 2026Article
- Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation.Chemical science · 2026Article
- Thiol-Free Sulfenylation Redefined: A Single-Atom Transfer Pathway to Symmetrical Di(hetero)arylthioethers via B(CJournal of the American Chemical Society · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
17 more citing papers are in PubMed but not listed here.
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Authors and funding
5 authors.
Funding
Abstract
Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.
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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.