CsF-Catalyzed Fluoroacylation of Tetrafluoroethylene Using Acyl Fluorides for the Synthesis of Pentafluoroethyl Ketones

Naoyoshi Ishida; Hiroaki Iwamoto; Denise Eimi Sunagawa; Masato Ohashi; Sensuke Ogoshi

doi:10.1055/s-0040-1705962

Synthesis, Table of Contents

Synthesis 2021; 53(17): 3137-3143
DOI: 10.1055/s-0040-1705962

special topic

Bond Activation – in Honor of Prof. Shinji Murai

CsF-Catalyzed Fluoroacylation of Tetrafluoroethylene Using Acyl Fluorides for the Synthesis of Pentafluoroethyl Ketones

Naoyoshi Ishida

,

Hiroaki Iwamoto

,

Denise Eimi Sunagawa

,

Masato Ohashi

,

Sensuke Ogoshi∗

Abstract

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Abstract

A catalytic method for the synthesis of pentafluoroethyl ketones has been developed. The cesium fluoride catalyst can be used to convert acyl fluorides into the pentafluoroethyl ketones under tetrafluoroethylene pressure without generating stoichiometric quantities of chemical waste. Mechanistic studies suggest that high reaction temperature is crucial for the ketone to be the major product.

Key words

acyl fluoride - tetrafluoroethylene - pentafluoroethyl ketone - pentafluoroethylation - cesium fluoride - DFT calculations

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References

References
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Supplementary Material

Supporting Information