Citation: 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 shu

Recent Progress of Protecting Groups for Terminal Alkynes

Hu Zhifang ^a ,
Peng Lifen ^a,b,, ,
Qiu Renhua ^b,, ,
Orita Akihiro ^c,,

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

Corresponding author: Peng Lifen, 1060137@hnust.edu.cn Qiu Renhua, renhuaqiu1@hnu.edu.cn Orita Akihiro, orita@dac.ous.ac.jp
Received Date: 31 May 2020
Revised Date: 2 July 2020
Available Online: 22 July 2020
Fund Project: 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)the National Natural Science Foundation of China 21802040the Open Foundation of Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology E21843the Natural Science Fund Youth Project of Hunan Province 2018JJ3145

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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.
- protecting group,
- terminal alkyne,
- Sonogashira coupling
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