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• W2950656429 abstract "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." @default.
• W2950656429 created "2019-06-27" @default.
• W2950656429 creator A5005484369 @default.
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• W2950656429 date "2019-06-20" @default.
• W2950656429 modified "2023-10-16" @default.
• W2950656429 title "Direct allylic C–H alkylation of enol silyl ethers enabled by photoredox–Brønsted base hybrid catalysis" @default.
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• W2950656429 doi "https://doi.org/10.1038/s41467-019-10641-y" @default.
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• W2950656429 hasPublicationYear "2019" @default.
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