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

doi:10.6023/cjoc201805009

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

Articles

膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔

彭丽芬^a, 彭超^a, 汪明^a, 唐子龙^a, 焦银春^a, 许新华^b

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 E-mail:1060137@hnust.edu.cn;zltang@hnust.edu.cn
基金资助:
国家自然科学基金（No.21402048）、湖南省自然科学基金（No.2018JJ3145）、湖南省教育厅一般项目（No.17C0629）、湖南科技大学博士启动基金（No.E51693）资助项目.

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

Peng Lifen^a, Peng Chao^a, Wang Ming^a, Tang Zilong^a, Jiao Yinchun^a, Xu Xinhua^b

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).

1. Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling.PDF(57674KB)

Abstract

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

Cite this article

Peng Lifen, Peng Chao, Wang Ming, Tang Zilong, Jiao Yinchun, Xu Xinhua. Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling[J]. Chin. J. Org. Chem., 2018, 38(11): 3048-3055.

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膦酰保护基促进选择性Hay偶联制备非对称1,3-二炔

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

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[2]	XIE, Ye-Xiang, LI, Jin-Heng, YIN, Du-Lin, JIANG, Huan-Feng. Palladium-Catalyzed Carbonylation of Acetylenes in Supercritical Carbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2004, 24(2): 169-172.