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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Lewis Acid Mediated Trifluoromethylthio Lactonization/Lactamization
1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
A novel Lewis acid-catalyzed reaction enables selective trifluoromethylthiolation of olefins, forming lactones and lactams. This method offers a new pathway for synthesizing valuable trifluoromethylthiolated compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Trifluoromethylthiolated compounds are important in medicinal chemistry and materials science.
- Efficient methods for introducing the trifluoromethylthio group are highly sought after.
Purpose of the Study:
- To develop a highly selective Lewis acid-mediated reaction for trifluoromethylthio lactonization and lactamization of olefins.
Main Methods:
- Reaction of olefins with a trifluoromethylthiolating agent in the presence of a Lewis acid.
- Proposed mechanism involving a thiiranium ion intermediate.
Main Results:
- Achieved highly selective formation of trifluoromethylthiolated lactones and lactams.
- Demonstrated the utility of Lewis acid catalysis in this transformation.
Conclusions:
- The described method provides an efficient route to valuable trifluoromethylthiolated heterocycles.
- The proposed thiiranium ion mechanism explains the observed selectivity.
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