ArticleScience advances2019
Ketones and aldehydes as alkyl radical equivalents for C─H functionalization of heteroarenes.
Article in Science advances, 2019. 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 16 papers.
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Who cites it
16 citing papers in PubMed.
- Vicinal disubstitution of alkyl C-X synthons via alkene radical cation generation.Science (New York, N.Y.) · 2026Article
- Redox-neutral ketone-olefin coupling enabled by mild ketone-to-ketyl-type radical conversion.Nature chemistry · 2026Article
- Electrochemical C4 alkylation of pyridine derivatives: Enhanced regioselectivity via silane assistance.Science advances · 2025Article
- Deoxygenative Cyanofunctionalization of Aldehydes and Ketones Enabled by Electrochemical Reduction.Journal of the American Chemical Society · 2025Article
- Cathodic tandem alkylation/dearomatization of heterocycles enabled by Al-facilitated carbonyl deoxygenation.Nature communications · 2025Article
- Catalytic Aldehyde-Alkyne Couplings Triggered by Ketyl Radicals.Organic letters · 2024Article
- Unraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C─H Functionalization via the Spin-Center Shift.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Acceptorless cross-dehydrogenative coupling for C(spCommunications chemistry · 2023Article
- Electrochemically Driven Deoxygenative Borylation of Alcohols and Carbonyl Compounds.Journal of the American Chemical Society · 2023Article
- Cobalt-electrocatalytic C-H hydroxyalkylation ofChemical science · 2022Article
- 1,2-Radical Shifts in Photoinduced Synthetic Organic Transformations: A Guide to the Reactivity of Useful Radical Synthons.ACS organic & inorganic Au · 2022Review
- Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.Angewandte Chemie (International ed. in English) · 2022Article
- Review
- Photocatalytic C(spChemical science · 2022Review
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Photocatalytic redox-neutral hydroxyalkylation ofChemical science · 2020Article
Corrections and comments
- Erratum issued
Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The polar nature of the C═O bond commonly allows it to undergo direct attack by nucleophiles at the electrophilic carbon atom in which ketones and aldehydes act as alkyl carbocation equivalents. In contrast, transformations in which ketones and aldehydes act as alkyl radical equivalents (generated in carbonyl carbon) are unknown. Here, we describe a new catalytic activation mode that combines proton-coupled electron transfer (PCET) with spin-center shift (SCS) and enables C─H alkylation of heteroarenes using ketones and aldehydes as alkyl radical equivalents. This transformation proceeded via reductive PCET activation of the ketones and aldehydes to form α-oxy radicals, addition of the radicals to the
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