Citation: Pang Xiaoyan, Ge Xin, Ji Jianye, Liang Weijie, Li Zhoujie, Chen Xunjun, Ge Jianfang. Progress in Silylation Protection and Deprotection of Hydroxyl Groups within Alcohol and Phenol[J]. Chemistry, ;2019, 82(1): 37-43. shu

Progress in Silylation Protection and Deprotection of Hydroxyl Groups within Alcohol and Phenol

1.
College of Chemical, ZhongKai University of Agriculture and Engineering, Guangzhou 510225
2.
School of Materials Science and Engineering, Northwestern Polytechnical University, Xi'an 710072

Corresponding author: Ge Jianfang, ge650704@163.com
Received Date: 31 July 2018
Accepted Date: 17 September 2018

Figures(2)

Silylation protection of hydroxyl groups within alcohol and phenol is an important class of organic synthesis, which means to stabilize the hydroxyl groups and eliminate or mitigate the side reactions caused by them. The smaller steric hindrance of the group attached to the silicon atom in the protecting group, the greater reactivity of the protecting group, and the worse stability of the corresponding silyl ether be formed. It can be removed under weak acid or weak base conditions. The larger steric hindrance of the group attached to the silicon atom, the smaller reactivity of the protecting group, and the more difficult of silylation reaction, which requires the use of a catalyst. This article describes the types of organosilane protecting groups, such as trimethylsilane, triethylsilane, tert-butyldimethylsilane, triisopropylsilane, phenyl-substituted silane and bridging silane. The activity and stability of the protecting group under different environments are also discussed.
- Silylation,
- Hydroxyl,
- Chemical reaction
1. [1]
2. [2]
3. [3]
4. [4]
5. [5]
6. [6]
  M C Pirrung, Y R Lee. USP:5486633. 1996.
7. [7]
  V G Kontogianni, P Charisiadis, A Primikyri et al. Org. Biomol. Chem, 2013, 11(6):1013~1025.
8. [8]
  F Popp, J B Natscher, J O Daiss et al. Organometallics, 2007, 26(24):6014~6028.
9. [9]
10. [10]
  G Aghapour, Z Abbaszadeh. Phosphorus Sulfur Silicon, 2015, 190(9):1464~1470.
11. [11]
  S T Kadam, S S Kim. Green Chem., 2010, 41(21):94~98.
12. [12]
  D Habibi, M Nasrollahzadeh. Synth. Commun., 2010, 40(21):3159~3167.
13. [13]
  S T Kadam, S S Kim. J. Organomet. Chem., 2009, 694(16):2562~2566.
14. [14]
  U Azzena, M Carraro, G Modugno et al. Beilstein J. Org. Chem., 2018, 14:1655~1659.
15. [15]
  B Zeynizadeh, S Sorkhabi. Phosphorus Sulfur Silicon, 2017, 193(3):127~135.
16. [16]
  A M Vibhute, K M Sureshan. Rsc Adv., 2013, 3(20):7321~7329.
17. [17]
18. [18]
19. [19]
  M Yadegari, M Moghadam. Appl. Organomet. Chem., 2016, 30(10):872~875.
20. [20]
21. [21]
  A Ziyaei-Halimjani, M R Saidi. J. Sci. (Iran), 2006, 17(2):123~126.
22. [22]
  B Thirupathi, A N Prasad, R Srinivas et al. Synth. Commun., 2011, 42(52):2064~2072.
23. [23]
  M Torki, S Tangestaninejad, V Mirkhani et al. Appl. Organomet. Chem., 2014, 28(4):304~309.
24. [24]
  H Tajik, K Niknam, S Karimian. Iran J. Catal., 2013, 3(2):107~113.
25. [25]
  H R Shaterian, M Ghashang. Phosphorus Sulfur Silicon, 2007, 183(1):194~204.
26. [26]
27. [27]
  M Jereb. Tetrahedron, 2012, 68(20):3861~3867.
28. [28]
  G Aghapour, A Kazemi Moghaddam, S Nadali. J. Chin. Chem. Soc-TAIP, 2015, 62(2):197~203.
29. [29]
  A Ghorbani-Choghamarani, N Cheraghi-Fathabad. Chin. J. Catal., 2010, 31(9):1103~1106.
30. [30]
  D Zareyee, R Asghari, M A Khalilzadeh. Chin. J. Catal., 2011, 32(11/12):1864~1868.
31. [31]
  H R Shaterian, F Khorami, A Amirzadeh et al. Phosphorus Sulfur Silicon, 2008, 183(10):2584~2595.
32. [32]
33. [33]
34. [34]
  M Sridhar, J Raveendra, B C Ramanaiah et al. Tetrahed. Lett., 2011, 52(45):5980~5982.
35. [35]
  A Abri, S Ranjdar. J. Chin. Chem. Soc-TAIP, 2014, 61(8):929~934.
36. [36]
37. [37]
38. [38]
  E J Corey, A Venkateswarlu. J. Am. Chem. Soc., 1972, 94(17):6190~6191.
39. [39]
40. [40]
  E L Bastos, L F M L Ciscato, W J Baader. Synth. Commun., 2005, 35(11):1501~1509.
41. [41]
  B S Gerstenberger, J P Konopelski. J. Org. Chem., 2005, 70(4):1467~1470.
42. [42]
  M Saudi, A Van Aerschot. Molecules, 2013, 18(7):8524~8534.
43. [43]
  P M Reis, B Royo. Catal. Commun., 2007, 8(7):1057~1059.
44. [44]
  H Liang, L Hu, E J Corey. Org. Lett., 2011, 13(15):4120~4123.
45. [45]
46. [46]
1. [1]
  Jie LEI , Xingfu YANG , Xiaoning TANG , Xu ZENG , Jie WEN , An XUE . Construction of highly stable zinc anodes induced by polyhydroxy inositol additives. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1627-1636. doi: 10.11862/CJIC.20260084
2. [2]
  Jiale Bai , Hongsheng Tang , Yaqian Zhou , Tianlong Zhang , Yan Li , Hua Li . 青铜器锈迹的化学解读. University Chemistry, 2026, 41(8): 203-209. doi: 10.12461/PKU.DXHX202508003
3. [3]
  Jingxuan Zhang , Weihao Jiang , Siyuan Zhang , Hongye Tian , Ziye Huang , Lin Huang , Qikun Wu , Jing Yang , Yibin Jiang , Cheng Wang . Automation and AI-Assisted Investigation of the Chemical Reactivity of Sulfosalicylic Acid. University Chemistry, 2026, 41(1): 332-345. doi: 10.12461/PKU.DXHX202505108
4. [4]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
5. [5]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
6. [6]
  Yang Lv , Yingping Jia , Yanhua Li , Hexiang Zhong , Xinping Wang . Integrating the Ideological Elements with the “Chemical Reaction Heat” Teaching. University Chemistry, 2024, 39(11): 44-51. doi: 10.12461/PKU.DXHX202402059
7. [7]
  Jian Huang , Mingjue Zhang , Shangchu Ma , Jia Dong , Guanzi Wu , Aiming Wen , Zhuoliang Liu . Data-Driven Approach for the Determination of Chemical Reaction Rate Constant. University Chemistry, 2026, 41(1): 213-226. doi: 10.12461/PKU.DXHX202505110
8. [8]
  Wenbo Liao , Jie Chao , Shaona Zheng , Lili Zhao , Xiaobo Fu . Reform and Practice of Ideological and Political Education in Chemical Reaction Engineering Courses. University Chemistry, 2026, 41(3): 233-241. doi: 10.12461/PKU.DXHX202504019
9. [9]
  Ming Chen , Zhenbo Mo . Research Progress on the Synthesis, Structure, and Chemical Reactivity of Borylenes. University Chemistry, 2026, 41(4): 250-263. doi: 10.12461/PKU.DXHX202502123
10. [10]
  Gengwei Zhang , Jun Cao . 化学反应动力学方程的AI辅助发现——以蔗糖水解反应为例. University Chemistry, 2026, 41(9): 396-404. doi: 10.12461/PKU.DXHX202508037
11. [11]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
12. [12]
  Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113
13. [13]
  Qihao Tang , Xiaohua Xin , Yunxia Wang , Han Wang . Mechanochemically Promoted Photochemical Reactions in Organic Synthesis. University Chemistry, 2026, 41(6): 321-327. doi: 10.12461/PKU.DXHX202503131
14. [14]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
15. [15]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
16. [16]
  Xuefei Zhao , Xuhong Hu , Zhenhua Jia . 理论与计算化学在傅-克烷基化反应教学中的应用. University Chemistry, 2025, 40(8): 360-367. doi: 10.12461/PKU.DXHX202410008
17. [17]
  Dexin Tan , Limin Liang , Baoyi Lv , Huiwen Guan , Haicheng Chen , Yanli Wang . Exploring Reverse Teaching Practices in Physical Chemistry Experiment Courses: A Case Study on Chemical Reaction Kinetics. University Chemistry, 2024, 39(11): 79-86. doi: 10.12461/PKU.DXHX202403048
18. [18]
  Ruming Yuan , Pingping Wu , Laiying Zhang , Xiaoming Xu , Gang Fu . Patriotic Devotion, Upholding Integrity and Innovation, Wholeheartedly Nurturing the New: The Ideological and Political Design of the Experiment on Determining the Thermodynamic Functions of Chemical Reactions by Electromotive Force Method. University Chemistry, 2024, 39(4): 125-132. doi: 10.3866/PKU.DXHX202311057
19. [19]
  Xuzhen Wang , Xinkui Wang , Dongxu Tian , Wei Liu . Enhancing the Comprehensive Quality and Innovation Abilities of Graduate Students through a “Student-Centered, Dual Integration and Dual Drive” Teaching Model: A Case Study in the Course of Chemical Reaction Kinetics. University Chemistry, 2024, 39(6): 160-165. doi: 10.3866/PKU.DXHX202401074
20. [20]
  Yawei Li , Siming Li , Fuhao Duan , Xuran Wang , Yangyang Zhao , Yue Zhang , Wei Guo , Junsheng Hao . 基于旋转电极双通道新方法的铁氰化钾电化学反应过程分析改进实验. University Chemistry, 2026, 41(5): 91-100. doi: 10.12461/PKU.DXHX202511082

Get Citation

PDF

XML

Metrics

PDF Downloads(103)
Abstract views(9707)
HTML views(1710)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142