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Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

Vera A. Vil’, Valentina M. Merkulova, Alexey I. Ilovaisky, Stanislav A. Paveliev, G. I. Nikishin, Alexander O. Terent’ev

2021Organic Letters42 citationsDOI

Abstract

Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

Topics & Concepts

EnolChemistryKetoneElectrosynthesisElectrochemistrySodiumOrganic chemistryCatalysisPhysical chemistryElectrodeFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions
Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates | Litcius