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Synthesis 2022; 54(01): 184-198
DOI: 10.1055/a-1561-5508
paper

Environmentally Friendly and Recyclable CuCl2-Mediated C–S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Guodong Shen∗
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Qichao Lu
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Zeyou Wang
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Weiwei Sun
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Yalin Zhang
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Xianqiang Huang∗
a   School of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China
,
Manman Sun
b   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China
,
Zhiming Wang
b   Advanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China
› InstitutsangabenThis work was financially supported by the Natural Science Foundation of Shandong Province (ZR2019QB022), the National Natural Science Foundation of China (21871125) and the Doctoral Scientific Research Startup Foundation of Liaocheng University (No. 31805403).
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Abstract

Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C–S bond-formation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N′-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.

Key words

environment friendly - recyclable - C–S bond coupling - DMEDA - CuCl2

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1561-5508.
  • Supporting Information


Publikationsverlauf

Eingereicht: 02. Juni 2021

Angenommen nach Revision: 29. Juli 2021

Accepted Manuscript online:
29. Juli 2021

Artikel online veröffentlicht:
09. September 2021

© 2021. Thieme. All rights reserved

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