ArticleNature communications2019
Direct allylic C-H alkylation of enol silyl ethers enabled by photoredox-Brønsted base hybrid catalysis.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 70 citations in OpenAlex.
- Photochemical Ring Opening of Cyclopropyl Silyl Ethers Enables β-β Coupling, Radical-Polar Crossover and Annulation.Angewandte Chemie (International ed. in English) · 2026Article
- Reductant-Free NiFThe Journal of organic chemistry · 2026Article
- Total Synthesis of Aconicarmisulfonine A, a Sulfonated Diterpene Alkaloid.Journal of the American Chemical Society · 2025Article
- Competing Michael/Anti-Michael Addition of Silyl Ketene Acetals to β-Nitrostyrenes Incorporating an Electron-Withdrawing Group.The Journal of organic chemistry · 2025Article
- Synergistic Copper-Aminocatalysis for Direct Tertiary α-Alkylation of Ketones with Electron-Deficient Alkanes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Expanding the chemical space of enol silyl ethers: catalytic dicarbofunctionalization enabled by iron catalysis.Chemical science · 2023Article
- Selective activation of four quasi-equivalent C-H bonds yields N-doped graphene nanoribbons with partial corannulene motifs.Nature communications · 2022Article
- Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2022Article
- A visible-light activated secondary phosphine oxide ligand enabling Pd-catalyzed radical cross-couplings.Nature communications · 2022Article
- Photoredox-Catalyzed C-H Functionalization Reactions.Chemical reviews · 2022Review
- Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones.Chemical science · 2021Article
- Benzylic C(spChemical science · 2021Article
- Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.Tetrahedron · 2021Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Strategies for altering the reaction pathway of reactive intermediates are of significant importance in diversifying organic synthesis. Enol silyl ethers, versatile enolate equivalents, are known to undergo one-electron oxidation to generate the radical cations that spontaneously form electrophilic α-carbonyl radicals via elimination of the silyl groups. Here, we demonstrate that close scrutiny of the property of the radical cations as strong C-H acids enables the identification of a catalyst system consisting of an iridium-based photosensitizer and 2,4,6-collidine for the generation of nucleophilic allylic radicals from enol silyl ethers through one-electron oxidation-deprotonation sequence under light irradiation without the desilylation of the radical cation intermediates. The resultant allylic radicals engage in the addition to electron-deficient olefins, establishing the selective allylic C-H alkylation of enol silyl ethers. This strategy is broadly applicable, and the alkylated enol silyl ethers can be transformed into highly functionalized carbonyl compounds by exploiting their common polar reactivity.
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