C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst

doi:10.6023/cjoc201410009

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 905-909.DOI: 10.6023/cjoc201410009 Previous Articles Next Articles

Notes

铜催化下苯并五元杂环化合物的C—S偶联反应

张变香, 陈凯, 杨丽花, 许钰涛, 张瑞杰, 张利娜, 史瑞雪

山西大学化学化工学院太原 030006

收稿日期:2014-10-09 修回日期:2014-12-03 发布日期:2014-12-10
通讯作者: 张变香 E-mail:zbxthh@sxu.edu.cn
基金资助:
山西省科技基础条件平台建设(No. 2013091026)、山西大学本科生科研训练(No. 2014013)资助项目.

C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst

Zhang Bianxiang, Chen Kai, Yang Lihua, Xu Yutao, Zhang Ruijie, Zhang Lina, Shi Ruixue

School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006

Received:2014-10-09 Revised:2014-12-03 Published:2014-12-10
Supported by:
Project supported by the Science and Technology Basic Conditions Platform Construction Project of Shanxi Province (No. 2013091026) and the Provincial Training Program of Innovation and Entrepreneurship for Undergraduates (No. 2014013).

1. C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst.PDF(488KB)

Abstract

In this study, the direct copper-catalyzed C—S coupling reaction of heterocyclic compounds with diphenyl disulfide, without the existence of ligands and alkalis, has been developed. It showed that the yield of target product was 89.9% when the reaction was carried out at 110 ℃, the reaction time was 12 h, dimethylsulfoxide (DMSO) was used as solvents, and the molar ratio of heterocyclic compound to biphenyl disulfide was 2:1. The structures of the target products were confirmed with ¹H NMR and ¹³C NMR. The effects of various conditions on the reaction were investigated by high performance liquid chromatography (HPLC) analysis and its reaction mechanism was discussed.

Key words: aryl thioether, benzo heterocyclic compounds, diphenyl disulfide, HPLC

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Zhang Bianxiang, Chen Kai, Yang Lihua, Xu Yutao, Zhang Ruijie, Zhang Lina, Shi Ruixue. C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst[J]. Chin. J. Org. Chem., 2015, 35(4): 905-909.

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铜催化下苯并五元杂环化合物的C—S偶联反应

C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst

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