Oxidation-Induced "One-Pot" Click Chemistry

被引:59
作者
Albada, Bauke [1 ]
Keijzer, Jordi F. [1 ]
Zuilhof, Han [1 ,2 ,3 ]
van Delft, Floris [1 ,4 ]
机构
[1] Wageningen Univ & Res, Lab Organ Chem, NL-6807 WE Wageningen, Netherlands
[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
[3] King Abdulaziz Univ, Fac Engn, Dept Chem & Mat Engn, Jeddah 21589, Saudi Arabia
[4] Synaffix BV, NL-5349 AE Oss, Netherlands
关键词
PROMOTED 1,3-DIPOLAR CYCLOADDITIONS; TRYPTOPHAN-CONTAINING PEPTIDES; SELECTIVE PROTEIN MODIFICATION; SITE-SPECIFIC CONJUGATION; PICTET-SPENGLER LIGATION; CROSS-LINKING; HORSERADISH-PEROXIDASE; PHOTOCLICK-CHEMISTRY; BIOORTHOGONAL REACTIONS; SURFACE MODIFICATION;
D O I
10.1021/acs.chemrev.0c01180
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Click chemistry has been established rapidly as one of the most valuable methods for the chemical transformation of complex molecules. Due to the rapid rates, clean conversions to the products, and compatibility of the reagents and reaction conditions even in complex settings, it has found applications in many molecule-oriented disciplines. From the vast landscape of click reactions, approaches have emerged in the past decade centered around oxidative processes to generate in situ highly reactive synthons from dormant functionalities. These approaches have led to some of the fastest click reactions know to date. Here, we review the various methods that can be used for such oxidation-induced "one-pot" click chemistry for the transformation of small molecules, materials, and biomolecules. A comprehensive overview is provided of oxidation conditions that induce a click reaction, and oxidation conditions are orthogonal to other click reactions so that sequential "click-oxidation-click" derivatization of molecules can be performed in one pot. Our review of the relevant literature shows that this strategy is emerging as a powerful approach for the preparation of high-performance materials and the generation of complex biomolecules. As such, we expect that oxidation-induced "one-pot" click chemistry will widen in scope substantially in the forthcoming years.
引用
收藏
页码:7032 / 7058
页数:27
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