高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (07): 1471-1475.doi: 10.3969/j.issn.0251-0790.2012.07.019

• 有机化学 • 上一篇    下一篇

系列烯基化芳香杂环化合物的合成及结构表征

张变香1, 杨祺1, 和潇夏1, 钞建宾2, 常姣1, 吴群1   

  1. 1. 山西大学化学化工学院, 太原 030006;
    2. 山西大学应用化学研究所, 太原 030006
  • 收稿日期:2011-10-11 出版日期:2012-07-10 发布日期:2012-07-10
  • 通讯作者: 张变香, 女, 博士, 副教授, 主要从事有机合成研究. E-mail: zbxthh@sxu.edu.cn E-mail:zbxthh@sxu.edu.cn
  • 基金资助:

    山西省回国留学人员科研资助项目(批准号: 2011-001)和山西省科学技术发展计划(工业攻关)项目(批准号: 20110321040-02)资助.

Synthesis and Characterization of a Series of Olefinated Aromatic Heterocyclic Compounds

ZHANG Bian-Xiang1, YANG Qi1, HE Xiao-Xia1, CHAO Jian-Bin2, CHANG Jiao1, WU Qun1   

  1. 1. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China;
    2. Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China
  • Received:2011-10-11 Online:2012-07-10 Published:2012-07-10

摘要: 报道了一个简单、 高选择性合成烯基化芳香杂环化合物的反应体系. 在钯的催化作用下, 以乙酸/乙酸酐或四氢呋喃为溶剂, 芳香杂环化合物与烯基化试剂进行交叉脱氢偶联, 合成了系列具有潜在光学活性的烯基化芳香杂环化合物, 确定了最佳反应条件. 采用紫外光谱、 核磁共振氢谱和X射线单晶衍射对目标化合物进行了表征, 并对反应机理进行了探讨.

关键词: 芳香杂环化合物, 烯基化试剂, 交叉脱氢偶联, X射线单晶衍射

Abstract: Heteroaromatic compounds are among the most important heterocyclic compounds. Olefinated aromatic heterocyclic compounds are important intermediates used not only as building blocks in the synthesis of natural products but also as key structural units of compounds with interesting biological activity. In this study, a series of olefinated aromatic heterocyclic compounds were prepared by palladium-catalyzed olefination via cross dehydrogenative coupling of C—H bonds. The effects of various conditions[5%(molar fraction) Pd(OAc)2, 60 ℃, 24 h] on the reaction were investigated by HPLC analysis. Their structures were determined by UV spectra, proton magnetic resonance and single crystal X-ray diffraction. The reaction was highly region- and stereoselective, giving trans-olefins predominantly by solvent controlled(AcOH/Ac2O), and its reaction mechanism was discussed.

Key words: Aromatic heterocyclic compound, Olefination, Cross dehydrogenative coupling, X-Ray single crystal diffraction

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