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Updated: Jun 29, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Triethyl amine as an effective reducing agent for sulfoxide deoxygenation
Xiaojing Gao1, Fumin Chen1, Ming Yu Jin1
1Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China. xuc@sustech.edu.cn.
A new chemical method efficiently converts sulfoxides to sulfides using triethyl amine and thionyl chloride. Triethyl amine acts as an electron donor, enabling a broad range of sulfoxide substrates for this deoxygenation reaction.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Sulfoxides are versatile functional groups in organic synthesis.
- Efficient deoxygenation of sulfoxides to sulfides is crucial for various chemical transformations.
Purpose of the Study:
- To develop a practical and efficient protocol for the deoxygenation of sulfoxides to sulfides.
- To investigate the reaction mechanism and the role of reagents involved.
Main Methods:
- Utilized triethyl amine (Et3N) and thionyl chloride (SOCl2) as key reagents.
- Employed a range of substituted sulfoxides (diaryl, dialkyl, aryl alkyl) to test substrate scope.
- Conducted detailed mechanistic investigations.
Main Results:
- An efficient and practical deoxygenation protocol was established.
- The method demonstrated a wide substrate scope, successfully converting various sulfoxide types.
- Mechanistic studies confirmed triethyl amine acts as an electron-donating reductant.
Conclusions:
- The developed protocol offers a valuable new method for sulfoxide to sulfide conversion.
- Understanding the reductive role of triethyl amine provides insight into the reaction mechanism.
- This method broadens the synthetic toolkit for accessing sulfide compounds.
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