Triethyl amine as an effective reducing agent for sulfoxide deoxygenation

Xiaojing Gao; Fumin Chen; Ming Yu Jin; Chen Xu

doi:10.1039/D4OB00219A

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Triethyl amine as an effective reducing agent for sulfoxide deoxygenation†

Xiaojing Gao,‡^a Fumin Chen,‡^a Ming Yu Jin*^a and Chen Xu

*^a

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* Corresponding authors

^a Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China
E-mail: xuc@sustech.edu.cn, jinmy@sustech.edu.cn

Abstract

Enabled by triethyl amine (Et₃N) and thionyl chloride (SOCl₂), an efficient and practical protocol for deoxygenation of sulfoxide to sulfide was developed. This new method features a wide range of substrate scope, including diaryl, dialkyl and aryl alkyl substituted sulfoxides. Detailed mechanistic investigations reveal the crucial role played by Et₃N as an electron-donating reductant rather than a hydrogen-atom donor.

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Article information

DOI: https://doi.org/10.1039/D4OB00219A
Article type: Communication
Submitted: 11 Feb 2024
Accepted: 26 Mar 2024
First published: 27 Mar 2024

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Org. Biomol. Chem., 2024,22, 3215-3219

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Triethyl amine as an effective reducing agent for sulfoxide deoxygenation

X. Gao, F. Chen, M. Y. Jin and C. Xu, Org. Biomol. Chem., 2024, 22, 3215 DOI: 10.1039/D4OB00219A

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Organic & Biomolecular Chemistry

Triethyl amine as an effective reducing agent for sulfoxide deoxygenation†

Abstract

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Triethyl amine as an effective reducing agent for sulfoxide deoxygenation

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