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

Guodong Shen; Qichao Lu; Zeyou Wang; Weiwei Sun; Yalin Zhang; Xianqiang Huang; Manman Sun; Zhiming Wang

doi:10.1055/a-1561-5508

Synthesis, Inhaltsverzeichnis

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∗

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Qichao Lu

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Zeyou Wang

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Weiwei Sun

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Yalin Zhang

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Xianqiang Huang∗

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, 1 Hunan Avenue, Liaocheng 252000, Shandong, P. R. of China

,

Manman Sun

^bAdvanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China

,

Zhiming Wang

^bAdvanced Research Institute and Department of Chemistry, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, Zhejiang, P. R. of China

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Abstract

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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

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