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New Electrophilic Trifluoromethylating Agents
Jing-Jing Yang1, Robert L. Kirchmeier, Jean'ne M. Shreeve
1Department of Chemistry, University of Idaho, Moscow, Idaho 83844-2343.
The Journal of Organic Chemistry
|October 24, 2001
Summary
New electrophilic trifluoromethylating agents were synthesized from phenyl trifluoromethyl sulfoxide. These stable sulfonium triflates efficiently trifluoromethylate various aromatic compounds under mild conditions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Electrophilic trifluoromethylation is a crucial transformation in organic synthesis.
- Development of stable and versatile trifluoromethylating reagents is of significant interest.
Purpose of the Study:
- To describe the synthesis of novel electrophilic trifluoromethylating agents.
- To investigate their reactivity with various aromatic substrates.
Main Methods:
- Synthesis of sulfonium triflates via reaction of phenyl trifluoromethyl sulfoxide with substituted benzenes.
- Trifluoromethylation of aromatic compounds including p-hydroquinone, pyrrole, and aniline.
Main Results:
- Stable sulfonium triflate derivatives (8-11) were successfully synthesized.
- These reagents effectively trifluoromethylated diverse aromatic rings, yielding products in moderate to high yields.
- Electron-withdrawing substituents on the benzene rings modulated the trifluoromethylating potential.
Conclusions:
- Novel, stable, and convenient electrophilic trifluoromethylating agents have been developed.
- These reagents offer a versatile method for introducing trifluoromethyl groups into aromatic systems.
- The electronic properties of the reagents can be tuned for specific applications.