ArticleJournal of the American Chemical Society2025
Carbon-Atom Scavengers Enable Divergent, Selective Carbon Deletion of Azaarenes.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
8 citing papers in PubMed.
- Embracing triplet nitrenes for C-to-N replacement of complex bicyclic (hetero)aryl azides.Science (New York, N.Y.) · 2026Article
- Emerging Strategies forJACS Au · 2026Review
- Photo-Stitching of Nitroalkanes via Cross-Denitrative Olefination.Journal of the American Chemical Society · 2026Article
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Photoinduced H-Bonding EDA complex-enabled skeletal editing of furans to pyridazines.Nature communications · 2026Article
- Mechanochemical Single-Carbon Insertion into (Iso)quinolines.Nature communications · 2026Article
- Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation.Chemical science · 2026Article
- Chiral hypervalent iodine catalyzed stereoselective skeletal editing of pyrimidine fused heterocycles.Nature communications · 2025Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors.
Funding
Abstract
Divergent synthesis is a powerful strategy that provides simultaneous access to multiple derivatives of a given substrate. However, the emerging developments in skeletal editing have largely delivered methods that lack this potential for diversification. Herein, we report the serendipitous discovery of reagent-controlled selective deletion of C3 or C2 carbon atoms of quinolines, affording indoles. An initial observation that an impurity in commercial samples of DBU promoted cyclization of a benzoxazepine-derived imidate led to the identification of indoline and aminoethanol as C3- and C2-selective carbon-atom scavengers, respectively. These two methods successfully convert a broad scope of quinolines and related azaarenes to the corresponding indoles and azaindoles, enabling divergent carbon deletion. In-depth mechanistic studies support the HFIP-promoted ring opening of 3,1-benzoxazepines to amidine intermediates as a rate-determining step, while providing insights into the selectivity afforded by indoline. These methods and their associated mechanisms offer a blueprint for the rational design of reagent-controlled, divergent skeletal edits.
Identifiers
What 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.