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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, Gennady I. Nikishin and Alexander O. Terent'ev*

*N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation, Email: terentevioc.ac.ru

V. A. Vil', V. M. Merkulova, A. I. Ilovaisky, S. A. Paveliev, G. I. Nikishin, A. O. Terent'ev, Org. Lett., 2021, 23, 5107-5112.

DOI: 10.1021/acs.orglett.1c01643


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Abstract

An electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions proceeds 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.

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proposed mechanism



Key Words

trifluoromethylation, electrochemistry


ID: J54-Y2021