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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3112 - 3119

DOI: https://doi.org/10.6023/cjoc202005094

Recent Progress of Protecting Groups for Terminal Alkynes

  • Hu Zhifang ,
  • Peng Lifen ,
  • Qiu Renhua ,
  • Orita Akihiro
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  • 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, Hunan 411201, China;
    b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;
    c Department of Chemistry, Okayama University of Science, Okayama 700-0005, Japan

Received date: 2020-05-31

  Revised date: 2020-07-02

  Online published: 2020-07-23

Supported by

Project supported by the National Natural Science Foundation of China (No. 21802040), the Natural Science Fund Youth Project of Hunan Province (No. 2018JJ3145) and the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology (No. E21843).

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Abstract

The protection/deprotection of functional group is one of the fundamental technologies in organic synthesis. An ideal protecting group needs to satisfy the following issues:facile introduction, stability and facile deprotection. Protection of an acetylenic hydrogen is often necessary because of its acidity. In this review, the recent progress of protecting groups for terminal alkyne is highlighted. Based on different polarity of protecting groups, less polar protecting groups such as trimethylsilyl (TMS), trimethylgermanium group (Me3Ge) and high polar protecting groups like (3-cyanopropyl)dimethylsilyl (CPDMS), (3-cyanopropyl)diisopropylsilyl (CPDIPS) and diphenylphosphoryl (Ph2P(O)) are introduced in detail.

Key words： protecting group; terminal alkyne; Sonogashira coupling

Cite this article

Hu Zhifang , Peng Lifen , Qiu Renhua , Orita Akihiro . Recent Progress of Protecting Groups for Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, 2020 , 40(10) : 3112 -3119 . DOI: 10.6023/cjoc202005094

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