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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (20): 2349-2354. 上一篇    下一篇

研究论文

双消除法一锅简便合成1－丙炔基芳香化合物

张志扬*,a    陈强b    安德烈*,b   

  1. (a西南大学化学化工学院 重庆 400715) (b湖南大学化学化工学院 长沙 410082)
  • 投稿日期:2009-01-14 修回日期:2009-05-06 发布日期:2009-06-10
  • 通讯作者: 张志扬 E-mail:zhyzhang@swu.edu.cn
  • 基金资助:

    西南大学博士基金(No. SWUB2008031)

Convenient Synthesis of (1-Propynyl)arenes through a One-Pot Double

Zhang, Zhiyang*,a       Chen, Qiangb       An, Delie*,b   

  1. (a School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715) (b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
  • Received:2009-01-14 Revised:2009-05-06 Published:2009-06-10

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报道了一种便捷合成1-丙炔基芳香化合物的新方法. 在充分探讨反应条件的基础上, 利用硫试剂乙基苯基砜与芳香醛组合, 采用双消除反应成功地一锅合成了一系列1-丙炔基芳香化合物1a～1s. 运用此法不仅合成出一些含有醚键、萘环、杂环以及含有两个1-丙炔基的化合物, 重要的是芳环上含有卤原子(Br和I)的化合物也能顺利地合成出来. 该方法原料易得, 操作简单, 产物容易分离纯化并且产率理想.

关键词: 1-丙炔基芳香化合物, 双消除反应, 一锅合成, 反应条件探讨

Presented here is a new convenient synthetic protocol to (1-propynyl)arenes. The synthesis methodology through one-pot double elimination procedure was developed based on detailed examination of the reaction condition. Reaction of ethyl phenyl sulfone with aryl aldehyde followed by a one-pot double elimination procedure afforded an array of (1-propynyl)arenes in moderate to good yields. Some products included methoxy group, naphthyl and heterocyclic aromatic moieties, and some were borne with two 1-propynyl groups. It is more important that compounds bearing halogens were also synthesized via this protocol. The virtues of this present protocol are facile available starting materials, convenient operation, and easy separation of desired products.

Key words: (1-propynyl)arene, double elimination reaction, one-pot synthesis, examination of reaction condition