过渡金属催化的1,2,3-三氮唑导向的C—H键官能团化反应研究进展  

Transition-metal Catalyzed 1,2,3-Triazole-assisted C—H Functionalization Processes

作　　者：刘霞[1] 匡春香[2] 苏长会 Liu Xia;Kuang Chunxiang;Su Changhui(Department of Environment and Ecology,Jiangsu Open University,Nanjing 210036;School of Chemical Science and Engineering,Tongjj University,Shanghai 200092;School of Chemistry and Life Sciences,Nanjing University Jinling College,Nanjing 210089)

机构地区：[1]江苏开放大学环境生态学院,南京210036 [2]同济大学化学科学与工程学院,上海200092 [3]南京大学金陵学院化学与生命科学学院,南京210089

出　　处：《化学学报》2022年第8期1135-1151,共17页Acta Chimica Sinica

基　　金：江苏开放大学国家级预研(No.19GY-Z-03)资助项目。

摘　　要：1,2,3-三氮唑化合物是一类具有重要生理活性的含氮杂环化合物,其在医药、农药、材料科学等领域都具有广泛的应用.不断开发基于三氮唑骨架的新型结构,寻找新型高效的合成三氮唑衍生物的方法具有重要的意义和应用价值.过渡金属催化的C—H键活化策略具有操作简便、效率高、三废少等优点,是现代有机合成中高效构筑C—C键和C—X键的强大工具.近年来,过渡金属催化的三氮唑导向的C—H官能团化反应受到科学工作者的广泛关注,该方法以不同结构的1,2,3-三氮唑作为导向基团,在不同反应条件下通过直接活化C—H键来构建新的C—C键和C—X键,高效合成复杂的三氮唑衍生物.综述了近年来1,2,3-三氮唑导向下过渡金属催化的C—H键官能团化反应研究进展,按照成键类型(碳-碳键、碳-杂键以及环化反应)对这些反应进行了梳理和总结,并对今后该领域的发展进行了展望.1,2,3-Triazole derivatives are a kind of N-containing heterocyclic compounds with important biological activities, which have widespread applications in diverse fields such as pharmaceuticals, pesticides, and materials. Therefore, it is of great significance to continuously develop new structures based on triazole framework and to find new and efficient synthetic methods of triazole derivatives. Although 1,2,3-triazole compounds are widely used, there is no report that 1,2,3-triazole compounds directly come from natural products. All of 1,2,3-triazoles and their dirivatives are artificially synthesized by chemical methods. Various strategies for their synthesis have been devised, with Huisgen 1,3-dipolar [3+2] cycloadditions of azides and alkynes being the most commonly used approach. However, this methodology, in most cases, leads to the formation of a mixture of regioisomeric products and requires the presence of a strong electron-withdrawing substitutent at the alkyne. Later, Fokin and Sharpless reported Cu(I)-catalyzed regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. This “click” reaction proceeded highly regioselectively when using terminal alkynes affording 1,4-disubstituted 1,2,3-triazoles in excellent yield. In recent years, transition-metal catalyzed C-H bond activation has attracted attention from scientists worldwide, and has become an important protocol for the construction of carbon-carbon bonds and carbon-heteroatom bonds in organic synthesis owing to its facile manipulation, high efficiency and less waste. An important strategy to realize the regioselectivity of the C-H activation is to use the auxiliary function of the directing group. Recently, transition-metal catalyzed 1,2,3-triazole-assisted C-H functionalization has been widely concerned by scientists. In this stragety, 1,2, 3-triazoles with different structures were used as guiding groups to construct new C-C and C-X bonds by direct conversion of C-H bonds under different reaction conditions to access more complex triazoles

关 键 词：1 2 3-三氮唑 C—H活化 过渡金属催化剂 有机合成 

分 类 号：O621.251[理学—有机化学]