ArticleAngewandte Chemie (International ed. in English)2016
Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Deprotonative Single-Electron Oxidation as a General and Controllably Selective Platform for Benzylic C-H Functionalization.Journal of the American Chemical Society · 2026Article
- Electrochemical Activation of α-Carbonyl Alkoxyamines for Direct Nucleophilic Substitution.Organic letters · 2026Article
- Iridium-Catalyzed Reductive Deoxygenation of Esters for the Synthesis of Sterically Hindered Ethers.Angewandte Chemie (International ed. in English) · 2025Article
- Organic photoredox-catalyzed unimolecular PCET of benzylic alcohols.Chemical science · 2025Article
- Iodide Anion Enables a Reductive Cross-Electrophile Coupling for Preparing Tertiary Amines.Angewandte Chemie (International ed. in English) · 2025Article
- Oxoammonium-Catalyzed Ether Oxidation via Hydride Abstraction: Methodology Development and Mechanistic Investigation Using Paramagnetic Relaxation Enhancement NMR.Journal of the American Chemical Society · 2024Article
- Accessing Alkoxy Radicals via Frustrated Radical Pairs: Diverse Oxidative Functionalizations of Tertiary Alcohols.Journal of the American Chemical Society · 2024Article
- Convergent approach for direct cross-coupling enabled by flash irreversible generation of cationic and anionic species.Nature communications · 2024Article
- Mechanistic studies on single-electron transfer in frustrated Lewis pairs and its application to main-group chemistry.Chemical Society reviews · 2024Review
- Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines.Journal of the American Chemical Society · 2024Article
- Consecutive π-Lewis acidic metal-catalysed cyclisation/photochemical radical addition promoted byChemical science · 2024Article
- Carbocationoids, a concept for controlling highly reactive cationic species.Communications chemistry · 2024Article
- Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer.ACS catalysis · 2024Article
- Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.Chemical science · 2023Article
- Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions.Nature communications · 2023Article
- Photoredox Catalysis-Enabled Sulfination of Alcohols and Bromides.Journal of the American Chemical Society · 2023Article
- OH radical-initiated single-electron transfer for accelerated degradationChemical science · 2023Article
- Molecular flavin catalysts for C-H functionalisation and derivatisation of dehydroamino acids.Chemical science · 2022Article
- Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.ACS catalysis · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
Corrections and comments
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3 authors.
Funding
Abstract
A new catalytic method is described to access carbocation intermediates via the mesolytic cleavage of alkoxyamine radical cations. In this process, electron transfer between an excited state oxidant and a TEMPO-derived alkoxyamine substrate gives rise to a radical cation with a remarkably weak C-O bond. Spontaneous scission results in the formation of the stable nitroxyl radical TEMPO(.) as well as a reactive carbocation intermediate that can be intercepted by a wide range of nucleophiles. Notably, this process occurs under neutral conditions and at comparatively mild potentials, enabling catalytic cation generation in the presence of both acid sensitive and easily oxidized nucleophilic partners.
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