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Palladium-Catalyzed Electrooxidative Hydrofluorination of Aryl-Substituted Alkenes with a Nucleophilic Fluorine Source.

Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes… Click to show full abstract

Herein, we report an electrocatalytic hydrofluorination of aryl-substituted alkenes with a nucleophilic fluorine source. The merger of palladium catalysis with electrooxidation enables the transformation of various substrates ranging from styrenes to more challenging α,β-unsaturated carbonyl derivatives to the corresponding benzylic fluorides. This method can also be applied to the late-stage modification of pharmaceutical derivatives. Mechanistic studies suggest that the generation of a high-valent palladium intermediate via anodic oxidation is the crucial step in this electrocatalytic hydrofluorination.

Keywords: alkenes nucleophilic; nucleophilic fluorine; hydrofluorination; hydrofluorination aryl; aryl substituted; substituted alkenes

Journal Title: Organic letters
Year Published: 2022

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