Redox-Neutral Tetrafluoroethylation of Aryl Alkynes with 1,1,2,2-Tetrafluoroethane Sulfonic Acid Leading to α-Tetrafluoroethylated Acetophenones

Takuji Kawamoto; Kohki Noguchi; Ryotaro Takata; Rio Sasaki; Hiroshi Matsubara; Akio Kamimura

doi:10.1002/chem.202100137

Redox-Neutral Tetrafluoroethylation of Aryl Alkynes with 1,1,2,2-Tetrafluoroethane Sulfonic Acid Leading to α-Tetrafluoroethylated Acetophenones

Chemistry. 2021 Jul 2;27(37):9529-9534. doi: 10.1002/chem.202100137. Epub 2021 May 17.

Authors

Takuji Kawamoto¹, Kohki Noguchi¹, Ryotaro Takata¹, Rio Sasaki¹, Hiroshi Matsubara², Akio Kamimura¹

Affiliations

¹ Department of Applied Chemistry, Yamaguchi University, Ube, Yamaguchi, 755-8611, Japan.
² Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka, 599-8531, Japan.

PMID: 33851767
DOI: 10.1002/chem.202100137

Abstract

The redox-neutral tetrafluoroethylation of alkynes with 1,1,2,2-tetrafluroroethanesulfonic acid (TFESA) and azobis(isobutyronitrile) (AIBN) proceeds via the formation of vinyl tetrafluoroethanesulfonates followed by a radical tetrafluoroethylation. Experimental and theoretical results support an intermolecular reaction.

Keywords: DFT calculations; radicals; reaction mechanisms; synthetic methods; tetrafluoroethylation.

MeSH terms

Acetophenones
Alkynes*
Hydrocarbons, Fluorinated
Oxidation-Reduction
Sulfonic Acids*

Substances

Acetophenones
Alkynes
Hydrocarbons, Fluorinated
Sulfonic Acids

Abstract

MeSH terms

Substances

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