铜催化下苯并五元杂环化合物的C—S偶联反应有机化学.pdfVIP

DOI: 10.6023/cjoc201410009 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 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) 摘要 以二苯二硫醚为硫源, 在无强碱和配体的条件下, 通过碘化亚铜催化促进 S—S 键断裂, 再与苯并五元杂环化合 1 13 物反应生成了芳基硫醚, 采用 H NMR 和 C NMR 对目标化合物进行了表征, 并确定了最佳反应条件. 在苯并五元杂 环化合物和二苯二硫醚的物质的量比为 2 ∶1, 催化剂 CuI 用量为 10 mol%, 溶剂为二甲基亚砜(DMSO), 反应温度 110 ℃, 时间 12 h 时, 产率达到 89.9%. 同时, 通过高效液相色谱(HLPC)进行跟踪监测, 对该反应的机理进行了探讨. 关键词 芳基硫醚; 苯并五元杂环; 二苯二硫醚; 高效液相色谱 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) Abstract In this study, the direct copper-catalyzed C—S coupling reaction of heterocyclic compounds with diphenyl disul- fide, 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 mech