ArticleAngewandte Chemie (International ed. in English)2022
Visible Light-Mediated Dearomative Hydrogen Atom Abstraction/ Cyclization Cascade of Indoles.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 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
14 citing papers in PubMed, 64 citations in OpenAlex.
- Dihydrobenzofuro[3,2-Chemical science · 2026Article
- Visible-Light-Mediated Lewis Acid-Catalyzed Diradical Hydrogen Atom Transfer Reaction of Enamides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Photochemical Cyclization of Tertiary Buta-2,3-dienamides to β-Lactams Upon Triplet Energy Transfer.Angewandte Chemie (International ed. in English) · 2026Article
- Visible-light-enabled excited-state dearomatization reactions.Science advances · 2026Review
- Photocatalysis as a mechanistic probe for the Staudinger β-lactam synthesis.Chem catalysis · 2025Article
- Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis.Nature communications · 2025Article
- Intramolecular Cobalt Porphyrin-Catalyzed Alkylation of 1-Isoindolinones by Site-Selective Insertion into a C(spOrganic letters · 2024Article
- Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines.ACS omega · 2024Review
- Photochemical dearomative skeletal modifications of heteroaromatics.Chemical Society reviews · 2024Review
- Mechanistic Investigation, Wavelength-Dependent Reactivity, and Expanded Reactivity ofJournal of the American Chemical Society · 2024Article
- Visible-Light-Mediated Energy Transfer Enables the Synthesis of β-Lactams via Intramolecular Hydrogen Atom Transfer.Angewandte Chemie (International ed. in English) · 2022Article
- Multicomponent Direct Assembly ofThe Journal of organic chemistry · 2022Article
- Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies.Journal of the American Chemical Society · 2022Article
- Visible Light-Mediated Dearomative Hydrogen Atom Abstraction/ Cyclization Cascade of Indoles.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The photochemical synthesis of yet unknown 2-oxospiro[azetidine-3,3'-indolines] (17 examples, 80-95 % yield), 2,4-dioxospiro[azetidine-3,3'-indolines] (eight examples, 87-97 % yield), and 1-oxo-1,3-dihydrospiro[indene-2,3'-indolines] (17 examples, 85-97 % yield) is described. Starting from readily accessible 3-substituted indoles, a dearomatization of the indole core was accomplished upon irradiation at λ=420 nm in the presence of thioxanthen-9-one (10 mol%) as the sensitizer. Based on mechanistic evidence (triplet energy determination, deuteration experiments, by-product analysis) it is proposed that the reaction proceeds by energy transfer via a 1,4- or 1,5-diradical intermediate. The latter intermediates are formed by excited state hydrogen atom transfer from suitable alkyl groups within the C3 substituent to the indole C2 carbon atom. Subsequent ring closure proceeds with pronounced diastereoselectivity to generate a 4- or 5-membered spirocyclic dearomatized product with several options for further functionalization.
Indexed as
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.