Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3048-3055.DOI: 10.6023/cjoc201805009 Previous Articles     Next Articles

Special Issue: 元素有机化学合辑2018-2019



彭丽芬a, 彭超a, 汪明a, 唐子龙a, 焦银春a, 许新华b   

  1. a 湖南科技大学化学化工学院 理论有机化学与功能分子教育部重点实验室 精细聚合物可控制备及功能化应用湖南省重点实验室 湘潭 411201;
    b 湖南大学化学化工学院 化学生物传感与计量学国家重点实验室 长沙 410082
  • 收稿日期:2018-05-02 修回日期:2018-05-30 发布日期:2018-07-05
  • 通讯作者: 彭丽芬, 唐子龙;
  • 基金资助:


Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling

Peng Lifena, Peng Chaoa, Wang Minga, Tang Zilonga, Jiao Yinchuna, Xu Xinhuab   

  1. a Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201;
    b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2018-05-02 Revised:2018-05-30 Published:2018-07-05
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21402048), the Natural Science Fund Youth Project of Hunan Province (No. 2018JJ3145), the General Project of Hunan Education Department (No. 17C0629) and the Doctoral Foundation of Hunan University of Science and Technology (No. E51693).

A selective Hay coupling reaction of aromatic terminal acetylenes and monophosphoryl-protected diynes was developed. The polarity of Ph2P(O) realized facile isolation of the desired unsymmetrical 1,3-diynes from by-products. The low reactivity of monophosphoryl-protected diynes reduced the oxidative homocoupling of itself and enhanced the yields of desired products. A number of aromatic terminal acetylenes and monophosphoryl-protected diynes were tolerated in this reaction, and all the corresponding unsymmetrical 1,3-diynes could be obtained in moderate to good yields. The unsymmetrical 1,3-diynes could be applied to synthesize unsymmetrical yne-diynes and cyclic polyynes.

Key words: Hay coupling, unsymmetrical 1,3-diyne, terminal acetylene, phosphoryl protecting group