Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

We present here a novel paired electrocatalysis-enabled convenient synthesis of the (<i>E</i>)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent <i>E</i> selectivity of products under metal- and oxidant-free conditions. A preliminary mechanistic study suggested that fluorinated sulfoximine generated from anodic oxidation of sulfinamide was the key intermediate that was then converted into the sulfonimidoyl radical at the cathode with the help of DBU in this reaction.

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Publication Details

Journal
Organic Letters
Published
2024-10-02
DOI
https://doi.org/10.1021/acs.orglett.4c02859
Citations
7
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
1.75

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article

Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

Dingguo Song, Weihui Zhong, Fei Ling, Tao Liu et al.
7 citations
Organic Letters
Synthesis and Catalytic Reactions
1.75
article

Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

Dingguo Song, Weihui Zhong, Fei Ling, Tao Liu, Kali Zhang, Jiyuan Guo, Yan Tang, Yunfei Hang, Changdi Zheng
article en
7 citations

Abstract

We present here a novel paired electrocatalysis-enabled convenient synthesis of the (<i>E</i>)-vinyl sulfoximines through the cross-coupling reaction of sulfinamides and olefins. This protocol showed a broad substrate scope and excellent <i>E</i> selectivity of products under metal- and oxidant-free conditions. A preliminary mechanistic study suggested that fluorinated sulfoximine generated from anodic oxidation of sulfinamide was the key intermediate that was then converted into the sulfonimidoyl radical at the cathode with the help of DBU in this reaction.

Organic LettersVol. 26(40)
Zhejiang Hisun Pharmaceutical (China) (CN), Zhejiang University of Technology (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Natural Science Foundation of Zhejiang Province
Clean water and sanitation
Openalex Percentile: Top 16%
Synthesis and Catalytic Reactions
1.75
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Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines — Dingguo Song, Weihui Zhong, et al. · Organic Letters (2024) | TGRS Research Map | TGRS