有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3112-3119.DOI: 10.6023/cjoc202005094 上一篇    下一篇

综述与进展

末端炔烃保护基的研究进展

胡志芳a, 彭丽芬a,b, 邱仁华b, 折田明浩c   

  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 湖南湘潭 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;
    c 日本冈山理科大学化学系 日本冈山 700-0005
  • 收稿日期:2020-05-31 修回日期:2020-07-02 发布日期:2020-07-23
  • 通讯作者: 彭丽芬, 邱仁华 E-mail:1060137@hnust.edu.cn;renhuaqiu1@hnu.edu.cn;orita@dac.ous.ac.jp
  • 基金资助:
    国家自然科学基金(No.21802040)、湖南省自然科学基金(No.2018JJ3145)、湖南科技大学理论有机化学与功能分子教育部重点实验室开放基金(No.E21843)资助项目.

Recent Progress of Protecting Groups for Terminal Alkynes

Hu Zhifanga, Peng Lifena,b, Qiu Renhuab, Orita Akihiroc   

  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, 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:2020-05-31 Revised:2020-07-02 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).

官能团的保护/脱保护是有机合成中最基础的技能之一,理想保护基需具备容易引入、稳定及容易脱保护等条件,末端炔烃中的氢原子具有一定酸性,在某些反应中往往需要先进行保护.综述了末端炔烃保护基的研究进展,对极性较小的保护基如三甲基硅基(TMS)、三甲基锗基(Me3Ge),极性较大的保护基如(3-氰基丙基)二甲基甲硅烷基(CPDMS)、(3-氰基丙基)二异丙基甲硅烷基(CPDIPS)和二苯基膦酰基(Ph2P(O))进行了详细介绍

关键词: 保护基, 末端炔烃, Sonogashira偶联

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