Chinese Journal of Organic Chemistry >
C—S Coupling Reaction of Heteroaromatic Compounds via Copper Catalyst
Received date: 2014-10-09
Revised date: 2014-12-03
Online 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).
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
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]. Chinese Journal of Organic Chemistry, 2015 , 35(4) : 905 -909 . DOI: 10.6023/cjoc201410009
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