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Synthesis 2021; 53(17): 3137-3143
DOI: 10.1055/s-0040-1705962
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
This work was supported by Japan Society for the Promotion of Science (JSPS KAKENHI) grants JP16H02276, JP17H03057, JP20K15278, and JP19J10485.
![](https://www.thieme-connect.de/media/synthesis/202117/lookinside/thumbnails/ss-2020-f0481-st_10-1055_s-0040-1705962-1.jpg)
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 calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705962.
- Supporting Information
Publikationsverlauf
Eingereicht: 08. September 2020
Angenommen nach Revision: 30. September 2020
Artikel online veröffentlicht:
28. Oktober 2020
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For a review of fluorinated ketones, see:
For selected examples for the synthesis of pentafluoroethyl ketones using pentafluoroethyl electrophiles, see:
For a review for fluorinated organometallics, see:
For selected examples for the synthesis of pentafluoroethyl ketones using pentafluoroethyl nucleophiles, see:
For selected examples of fluoroalkylation reactions of aromatic compounds, see:
For selected examples of fluoroakylation reactions of fluoroformates or acyl fluorides bearing a perfluoroalkyl moiety, see: