ArticleJournal of the American Chemical Society2023
Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
What it found
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Who cites it
18 citing papers in PubMed.
- Cooperative Brønsted Acid and Photo-Promoted Stereoselective Synthesis of Substituted Piperidones.Angewandte Chemie (International ed. in English) · 2025Article
- Photochemical Insights on Acyl Azolium Salts Enable the Design of a Tandem Hydrogen Atom Transfer/Halogen Atom Transfer Acylation of Alkyl Bromides and Chlorides.Journal of the American Chemical Society · 2025Article
- N-Heterocyclic Carbene Stabilized Bisacylgermylenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Photobiocatalytic Enantioselective Benzylic C(spJournal of the American Chemical Society · 2025Article
- Photochemical reduction of acylimidazolium salts.Beilstein journal of organic chemistry · 2025Article
- Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.ACS catalysis · 2024Article
- Highly Efficient Photoinitiation Systems Based on Dibenzo[a,c]phenazine Sensitivity to Visible Light for Dentistry.Materials (Basel, Switzerland) · 2024Article
- Design of Dyes Based on the Quinoline or Quinoxaline Skeleton towards Visible Light Photoinitiators.International journal of molecular sciences · 2024Article
- Mechanistic Investigation, Wavelength-Dependent Reactivity, and Expanded Reactivity ofJournal of the American Chemical Society · 2024Article
- Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis.Molecules (Basel, Switzerland) · 2024Article
- Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024Article
- Photoinduced cerium-catalyzed C-H acylation of unactivated alkanes.Chemical science · 2023Article
- Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.Angewandte Chemie (International ed. in English) · 2023Article
- Photoredox-Catalyzed Radical-Radical Coupling of Potassium Trifluoroborates with Acyl Azoliums.Synlett : accounts and rapid communications in synthetic organic chemistry · 2023Article
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
- Article
- Acyl Azolium-Photoredox-Enabled Synthesis ofACS catalysis · 2023Article
- A (TD-)DFT study on photo-NHC catalysis: photoenolization/Diels-Alder reaction of acid fluorides catalyzed byChemical science · 2023Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Photoinduced hydrogen atom transfer (HAT) has been developed as a powerful tool to generate synthetically valuable radical species. The direct photoexcitation of ketones has been known to promote HAT or to generate acyl radicals through Norrish-type pathways, but these modalities remain severely limited by radical side reactions. We report herein a catalyst- and transition metal-free method for the acylation of C-H bonds that leverages the unique properties of stable, isolable acyl azolium species. Specifically, acyl azolium salts are shown to undergo an intermolecular and regioselective HAT upon LED irradiation with a range of substrates bearing active C-H bonds followed by C-C bond formation to afford ketones. Experimental and computational studies support photoexcitation of the acyl azolium followed by facile intersystem crossing to access triplet diradical species that promote selective HAT and radical-radical cross-coupling.
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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.