Photoredox-Catalyzed Reductive Carbamoyl Radical Generation: A Redox-Neutral Intermolecular Addition–Cyclization Approach to Functionalized 3,4-Dihydroquinolin-2-ones

The first reductive generation of carbamoyl radicals using photoredox catalysis for their formation is reported. This approach facilitated the development of a redox-neutral synthesis of functionalized 3,4-dihydroquinolin-2-ones via the novel intermolecular addition–cyclization of carbamoyl radicals...

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Bibliographic Details
Published in:Organic letters 2017-02, Vol.19 (4), p.874-877
Main Authors: Petersen, Wade F, Taylor, Richard J. K, Donald, James R
Format: Article
Language:English
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Summary:The first reductive generation of carbamoyl radicals using photoredox catalysis for their formation is reported. This approach facilitated the development of a redox-neutral synthesis of functionalized 3,4-dihydroquinolin-2-ones via the novel intermolecular addition–cyclization of carbamoyl radicals across electron-deficient alkenes. To illustrate the versatility of this reaction, a diverse collection of 3,4-dihydroquinolin-2-ones, including fused cyclic and spirocyclic systems inspired by natural products, has been prepared.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00022