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General, Practical and Selective Oxidation Protocol for CF₃S into CF₃S(O) Group
Liubov V Sokolenko1, Raisa K Orlova2, Andrey A Filatov3
1Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmans'ka Str. 5, 02094 Kyiv, Ukraine. sokolenko.liubov@gmail.com.
Molecules (Basel, Switzerland)
|April 3, 2019
Summary
A new method efficiently oxidizes trifluoromethyl, mono-, and difluoromethyl sulfides to sulfoxides. This process, using trifluoroperacetic acid (TFPAA), avoids over-oxidation to sulfones and works for various substrates.
Area of Science:
- Organic Chemistry
- Oxidation Reactions
Background:
- Selective oxidation of organofluorine sulfides is challenging.
- Over-oxidation to sulfones is a common side reaction.
Purpose of the Study:
- To develop a simple and efficient protocol for oxidizing trifluoromethyl, mono-, and difluoromethyl sulfides.
- To achieve selective oxidation to sulfoxides without forming sulfones.
Main Methods:
- In situ preparation of trifluoroperacetic acid (TFPAA) from trifluoroacetic acid and hydrogen peroxide.
- Oxidation of various aromatic and aliphatic trifluoromethyl, mono-, and difluoromethyl sulfides.
Main Results:
- Successful oxidation of target sulfides to corresponding sulfoxides.
- No over-oxidation to sulfones observed.
- Method demonstrated on milligram and multigram scales.
Conclusions:
- A straightforward and effective protocol for selective sulfide oxidation was established.
- The developed method offers a reliable route to fluorinated sulfoxides.
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