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

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-04 DOI:10.1002/ejoc.202401467
Xinyu Zhang, Rutian Sun, Daming Zeng, Prof. Dr. Ming Wang, Prof. Dr. Xuefeng Jiang
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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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铜催化的双侧亚砜胺键构建环亚砜胺
采用cui催化的方法,建立了s -苯乙基亚砜胺与环二芳硫鎓盐的双边连锁反应,一步合成环亚砜胺。具有挑战性的环亚砜胺可以通过后续氧化有效地获得。光物理性质和DFT计算表明,与环亚胺和砜相比,环亚胺具有更大的斯托克斯位移和更少的HOMO-LUMO轨道重叠。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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