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Radical Acylfluoroalkylation of 1,3-Enynes via <i>N</i>-Heterocyclic Carbene/Photoredox Cooperative Catalysis

Shichao Tian, Ning Chen, Keguang Cheng, Quande Wang

2024Organic Letters12 citationsDOI

Abstract

-heterocyclic carbene (NHC)/photoredox catalysis toward various fluorinated allenic aryl ketones. This protocol features a broad substrate scope and excellent functional group tolerability, with examples of late-stage modification of drug molecules and natural products. Notably, seven different fluoroalkyl motifs can be introduced to 1,3-enynes, further demonstrating the robustness and generality of this method. The generation of the fluoroalkyl radical from each sulfinate reagent was individually supported by EPR experiments.

Topics & Concepts

CarbeneChemistryCatalysisPhotoredox catalysisMedicinal chemistryCombinatorial chemistryPhotochemistryOrganic chemistryPhotocatalysisFluorine in Organic ChemistryRadical Photochemical Reactions
Radical Acylfluoroalkylation of 1,3-Enynes via <i>N</i>-Heterocyclic Carbene/Photoredox Cooperative Catalysis | Litcius