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Molecules. 2019 Mar 30;24(7). pii: E1249. doi: 10.3390/molecules24071249.

General, Practical and Selective Oxidation Protocol for CF₃S into CF₃S(O) Group.

Author information

1
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans'ka Str. 5, 02094 Kyiv, Ukraine. sokolenko.liubov@gmail.com.
2
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans'ka Str. 5, 02094 Kyiv, Ukraine. OrlovaRaisa@ukr.net.
3
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans'ka Str. 5, 02094 Kyiv, Ukraine. filatov@ioch.kiev.ua.
4
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans'ka Str. 5, 02094 Kyiv, Ukraine. yagupolskii@ioch.kiev.ua.
5
Enamine Ltd, A. Matrosova str. 23, Kiev 01103, Ukraine. yagupolskii@ioch.kiev.ua.
6
Bâtiment Lavoisier, Université de Versailles-Saint-Quentin, 45 avenue des Etats-Unis, 78035 Versailles, France. emmanuel.magnier@uvsq.fr.
7
Bâtiment Lavoisier, Université de Versailles-Saint-Quentin, 45 avenue des Etats-Unis, 78035 Versailles, France. bruce.pegot@uvsq.fr.
8
Bâtiment Lavoisier, Université de Versailles-Saint-Quentin, 45 avenue des Etats-Unis, 78035 Versailles, France. patrick.diter@uvsq.fr.

Abstract

A simple and efficient protocol for the oxidation of trifluoromethyl, mono- and difluoromethyl sulfides to the corresponding sulfoxides without over-oxidation to sulfones, using TFPAA prepared in situ from trifluoroacetic acid and 15% H₂O₂ aqueous solution was developed. The methodology is suitable for a wide range of aromatic and aliphatic substrates in milligram and multigram scales.

KEYWORDS:

dihydrogen peroxide; oxidation; trifluoromethylsulfides; trifluoromethylsulfoxides; trifluoroperacetic acid

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