Cu‐catalyzed Bilateral Linkage of Sulfenamides for the Construction of Benzothiophene‐based Cyclic Sulfilimines

Abstract A CuI‐catalyzed bilateral linkage of S ‐phenethyl‐sulfenamides with cyclic diaryliodonium salts was developed for the one‐step construction of benzothiophene‐based cyclic sulfilimines. The challenging cyclic sulfoximines can be efficiently obtained via subsequent oxidation. Photophysical properties and DFT calculations reveal that cyclic sulfoximines, compared to cyclic sulfilimines and sulfones, exhibit larger Stokes shifts and reduced HOMO‐LUMO orbital overlap.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-02-04
DOI
https://doi.org/10.1002/ejoc.202401467
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
3.74
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article

Cu‐catalyzed Bilateral Linkage of Sulfenamides for the Construction of Benzothiophene‐based Cyclic Sulfilimines

Daming Zeng, Ming Wang, Rutian Sun, Xuefeng Jiang et al.
4 citations
European Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
3.74
article

Cu‐catalyzed Bilateral Linkage of Sulfenamides for the Construction of Benzothiophene‐based Cyclic Sulfilimines

Daming Zeng, Ming Wang, Rutian Sun, Xuefeng Jiang, Xinyu Zhang
article en
4 citations

Abstract

Abstract A CuI‐catalyzed bilateral linkage of S ‐phenethyl‐sulfenamides with cyclic diaryliodonium salts was developed for the one‐step construction of benzothiophene‐based cyclic sulfilimines. The challenging cyclic sulfoximines can be efficiently obtained via subsequent oxidation. Photophysical properties and DFT calculations reveal that cyclic sulfoximines, compared to cyclic sulfilimines and sulfones, exhibit larger Stokes shifts and reduced HOMO‐LUMO orbital overlap.

European Journal of Organic ChemistryVol. 28(16)
Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), East China Normal University (CN), Henan Normal University (CN)
Openalex Percentile: Top 9%
Sulfur-Based Synthesis Techniques
3.74
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Cu‐catalyzed Bilateral Linkage of Sulfenamides for the Construction of Benzothiophene‐based Cyclic Sulfilimines — Daming Zeng, Ming Wang, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS