ArticleNature chemistry2024
Tunable molecular editing of indoles with fluoroalkyl carbenes.
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.
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- Reprogramming RiPP scaffolds through skeletal editing unlocks chemical space.Chemical science · 2026Article
- Decoding skeletal diversity and complexity: A biomimetic and photochemical remodeling strategy.Science advances · 2026Article
- A difluorocarbene-triggered annulation/ring expansion cascadeChemical science · 2026Article
- Merging photocatalysis with C-H insertions enabled switchable synthesis of indoles and indolines.Nature communications · 2026Article
- Facile Synthesis of Nonalternant π-Conjugated Azaborines via Boron-Deleting Annulation.Journal of the American Chemical Society · 2026Article
- Study on the structural characteristics of nitrogen-containing compounds in co-pyrolysis tar of low rank coal usingScientific reports · 2026Article
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
- Thermal [2+2] cycloaddition as a route to gem-difluoro heterobicyclo[n.1.1]alkanes.Nature chemistry · 2026Article
- Enantioselective dearomative single-atom skeletal editing of benzofurans.Nature communications · 2025Article
- Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.JACS Au · 2025Article
- Rh-Catalyzed Atroposelective Single-Carbon Insertion.Journal of the American Chemical Society · 2025Article
- Single-carbon-atom transfer toChemical science · 2025Article
- [2,3]-Sigmatropic rearrangement with [1.1.1]propellane.Nature communications · 2025Article
- Switchable skeletal editing of quinolines enabled by cyclizative sequential rearrangements.Nature chemistry · 2025Article
- Divergent and Enantioselective Synthesis of Three Types of Chiral Polycyclic N‑Heterocycles via Copper-Catalyzed Dearomative Cyclization.ACS central science · 2025Article
- Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions.ACS central science · 2025Article
- Fluorescent pyridine phosphonium salts via transmutation of metallabenzenes.Nature communications · 2025Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Building molecular complexity from simple feedstocks through precise peripheral and skeletal modifications is central to modern organic synthesis. Nevertheless, a controllable strategy through which both the core skeleton and the periphery of an aromatic heterocycle can be modified with a common substrate remains elusive, despite its potential to maximize structural diversity and applications. Here we report a carbene-initiated chemodivergent molecular editing of indoles that allows both skeletal and peripheral editing by trapping an electrophilic fluoroalkyl carbene generated in situ from fluoroalkyl N-triftosylhydrazones. A variety of fluorine-containing N-heterocyclic scaffolds have been efficiently achieved through tunable chemoselective editing reactions at the skeleton or periphery of indoles, including one-carbon insertion, C3 gem-difluoroolefination, tandem cyclopropanation and N1 gem-difluoroolefination, and cyclopropanation. The power of this chemodivergent molecular editing strategy has been highlighted through the modification of the skeleton or periphery of natural products in a controllable and chemoselective manner. The reaction mechanism and origins of the chemo- and regioselectivity have been probed by both experimental and theoretical methods.
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38443494What OpenQuestion holds
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.