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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (14): 1688-1696. 上一篇    下一篇

研究论文

5-取代-3,4-二卤-2(5H)-呋喃酮的Sonogashira偶联反应

李建晓，薛福玲，谭越河，罗时荷，汪朝阳*   

  1. (华南师范大学化学与环境学院 广州 510006)
  • 投稿日期:2010-12-24 修回日期:2011-02-24 发布日期:2011-03-03
  • 通讯作者: 汪朝阳 E-mail:wangwangzhaoyang@tom.com
  • 基金资助:

    国家自然科学基金

Sonogashira Coupling Reaction of 5-Substituted 3,4-Dihalo-2(5H)-furanones

LI Jian-Xiao, XUE Fu-Ling, TAN Yue-He, LUO Shi-He, WANG Chao-Yang   

  1. (School of Chemistry and Environment, South China Normal University, Guangzhou 510006)
  • Received:2010-12-24 Revised:2011-02-24 Published:2011-03-03
  • Contact: Zhaoyang Wang E-mail:wangwangzhaoyang@tom.com
  • Supported by:

    the National Natural Science Foundation of China

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被引次数

19

以5-取代-3,4-二卤-2(5H)-呋喃酮为底物进行Sonogashira偶联反应, 考察了反应温度、反应时间、钯催化剂种类与用量、碱种类与用量、溶剂、底物结构等对偶联反应的影响, 合成了28种新的2(5H)-呋喃酮衍生物, 其结构用IR, 1H NMR, 13C NMR, MS和元素分析等方法进行了表征. 在优化的反应条件下, 即反应溶剂为甲苯、催化剂为3 mol% Pd(PPh3)4和10 mol% CuI、碱为6 equiv. KF、反应时间72 h、反应温度30 ℃时, 反应产率42%～84%. 利用该Sonogashira偶联反应合成新型的多官能团烯二炔结构化合物, 不仅合成途径简捷、反应条件温和, 绝大部分反应产率中等以上, 而且无需额外加入配体, 适用于芳香的和脂肪的末端炔烃.

关键词: 5-取代-3,4-二卤-2(5H)-呋喃酮, 末端炔烃, Sonogashira偶联, 烯二炔

Using 5-substituted 3,4-dihalo-2(5H)-furanones as the substrates, the Sonogashira coupling reaction in the presence of palladium catalyst gave 28 novel compounds. The structure was confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. The influences of reaction temperature and time, catalyst kinds and dosage, base kinds and dosage, solvent, and different substrates were investigated. Under the optimized conditions, including 3 mol% Pd(PPh3)4 as the catalyst and 10 mol% CuI as the cocatalyst, 6.0 equiv. KF as the base, toluene as the solvent, the cross-coupling reactions with propargylic alcohol, as well as terminal alkyl and aryl alkynes at 30 ℃ for 72 h gave the 2(5H)-furanone derivatives containing enediyne structure in moderate to good yields without the addition of other ligands.

Key words: 5-substituted 3,4-dihalo-2(5H)-furanone, terminal alkyne, Sonogashira coupling reaction, enediyne