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; Alexander O Terent'ev

doi:10.1021/acs.orglett.1c01643

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

Org Lett. 2021 Jul 2;23(13):5107-5112. doi: 10.1021/acs.orglett.1c01643. Epub 2021 Jun 14.

Authors

Vera A Vil'¹, Valentina M Merkulova¹, Alexey I Ilovaisky¹, Stanislav A Paveliev¹, Gennady I Nikishin¹, Alexander O Terent'ev¹

Affiliation

¹ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.

PMID: 34124913
DOI: 10.1021/acs.orglett.1c01643

Abstract

The electrochemical synthesis of fluorinated ketones from enol acetates and R_fSO₂Na 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%.

Publication types

Research Support, Non-U.S. Gov't