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化学进展 2016, Vol. 28 Issue (4): 507-527 DOI: 10.7536/PC150825 前一篇   后一篇

• 综述与评论 •

1,3-二炔的合成

江玉波1, 刘耀文1, 张文生2, 成会玲1, 匡春香3, 陈阵1*   

  1. 1. 昆明理工大学理学院 昆明 650500;
    2. 焦作师范高等专科学校理工学院 焦作 454000;
    3. 同济大学化学系 上海 200092
  • 收稿日期:2015-08-01 修回日期:2015-09-01 出版日期:2016-04-15 发布日期:2016-01-17
  • 通讯作者: 陈阵 E-mail:chenzhen69@qq.com
  • 基金资助:
    国家自然科学基金项目(No. 51464021)资助
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Synthesis of 1,3-Diynes

Jiang Yubo1, Liu Yaowen1, Zhang Wensheng2, Cheng Huiling1, Kuang Chunxiang3, Chen Zhen1*   

  1. 1. Faculty of Science, Kunming University of Science and Technology, Kunming 650500, China;
    2. School of Science and Technology, Jiaozuo Teachers' College, Jiaozuo 454000, China;
    3. Department of Chemistry, Tongji University, Shanghai 200092, China
  • Received:2015-08-01 Revised:2015-09-01 Online:2016-04-15 Published:2016-01-17
  • Supported by:
    The work was supported by the National Natural Science Foundation of China(No. 51464021).
随着1,3-二炔类化合物在有机合成及功能材料等领域的广泛应用,它的合成引起了广大研究者的关注.本文阐述了1,3-二炔类化合物的合成发展历史,着重综述了近十年来1,3-二炔类化合物的合成发展情况,按原料类别进行介绍,主要包括以末端炔、炔基卤化物、金属炔化物和烯基卤化物等为原料合成1,3-二炔化合物的新成果.文章还分析了一些合成方法在医药领域的应用和重要的反应机理,并总结了该类化合物的合成及未来发展方向.
关键词： 1,3-二炔, 末端炔, 炔基卤化物, 金属炔化物, 烯基卤化物
Much attention has been paid to the synthesis of 1,3-diynes with the development of its wide applications in the fields of organic synthesis and functional materials. This review describes the synthesis history of the 1,3-diynes and emphatically the synthesis development of 1,3-diynes in recent 10 years. It introduces the new achievements in synthesis of 1,3-diynes from its starting materials including terminal alkynes, alkynyl halides, metal acetylides, alkenyl halides, and other precursors. Medical applications of some reactions and relevant mechanisms are also described in this paper. Finally, the synthesis of 1,3-diynes is concluded and the development trends in the field of 1,3-diynes synthesis are proposed.

Contents
1 Introduction
2 Synthesis from terminal alkynes
2.1 Catalyzed by Pd-Cu
2.2 Catalyzed by Pd
2.3 Catalyzed by Cu
2.4 Other methods from terminal alkynes
3 Synthesis from alkynyl halides
4 Synthesis from metal acetylides
5 Synthesis from alkenyl halides
6 Other methods
7 Conclusion

Key words: 1,3-diyne, terminal alkyne, alkynyl halides, metal acetylides, alkenyl halide

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[1] 雷朋飞, 张文生, 匡春香, 江玉波. 芳基末端炔的合成[J]. 化学进展, 2016, 28(2/3): 317-327.
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摘要

1,3-二炔的合成