ArticleJournal of the American Chemical Society2022
Radicals as Exceptional Electron-Withdrawing Groups: Nucleophilic Aromatic Substitution of Halophenols Via Homolysis-Enabled Electronic Activation.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 46 citations in OpenAlex.
- Synergistic Fe/Ni catalysis for electrochemical 1,1-difunctionalization of alkenes.Nature communications · 2026Article
- Photocatalytic Cross-Coupling of Phenols and Heteroaryl Halides With Machine Learning-Guided Reaction Prediction.Angewandte Chemie (International ed. in English) · 2026Article
- A 4,4',4″-nitrilotriphenoxyl radical derived from Yang's biradical.Chemical science · 2026Article
- Harnessing redox properties of organic persistent radicals in SET-induced transformations.Beilstein journal of organic chemistry · 2026Review
- Electrochemically promoted defluorinative sulfoximination and fluorosulfonylation of non-activated aryl fluorides at room temperature.Chemical science · 2025Article
- Photoredox-Catalyzed Nucleophilic Aromatic Substitution of Halophenols with Azoles via Oligomeric Phenylene Oxide Radicals.Journal of the American Chemical Society · 2025Article
- Article
- Radical Polarity.Journal of the American Chemical Society · 2024Article
- Diversification of Bipyridines and Azaheterocycles via Nucleophilic Displacement of Trimethylammoniums.ACS organic & inorganic Au · 2024Article
- Amination of Phenols and Halophenols via Pyridinium-Iridium Dual Photocatalysis.ACS catalysis · 2024Article
- Stereoselective Polymerization of 3,6-DisubstitutedACS macro letters · 2024Article
- Universal inter-molecular radical transfer reactions on metal surfaces.Nature communications · 2024Article
- Synthesis of Phenol-Pyridinium Salts Enabled by Tandem Electron Donor-Acceptor Complexation and Iridium Photocatalysis.The Journal of organic chemistry · 2024Article
Corrections and comments
- Erratum issued
Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
While heteroatom-centered radicals are understood to be highly electrophilic, their ability to serve as transient electron-withdrawing groups and facilitate polar reactions at distal sites has not been extensively developed. Here, we report a new strategy for the electronic activation of halophenols, wherein generation of a phenoxyl radical via formal homolysis of the aryl O-H bond enables direct nucleophilic aromatic substitution of the halide with carboxylate nucleophiles under mild conditions. Pulse radiolysis and transient absorption studies reveal that the neutral oxygen radical (O
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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.