经典“点击反应”中间体在合成化学中的应用进展--1,2,3-三唑-5-铜(Ⅰ)构建碳-碳键

Application Advanced of Classical“Click Reaction”Intermediate in Synthetic Chemistry:Application of 1,2,3-Triazol-5-Copper(Ⅰ)in the Construction of Carbon-carbon Bonds

最经典的“点击反应”是铜(Ⅰ)催化末端炔和有机叠氮化合物的[3+2]环加成(CuAAC)高选择性地合成1,4-二取代1,2,3-三唑五元杂环化合物的反应。该反应作为一种强大的工具被广泛应用于合成化学及生物化学。基于CuAAC的潜在价值,总结了CuAAC的关键中间体——1,2,3-三唑-5-铜(Ⅰ)在构建碳-碳键中的应用进展,包括利用该中间体构建C(sp^(2))-C(sp ^(3))键,C(sp^(2))-C(sp^(2))键和C(sp^(2))-C(sp)键的反应机理和应用,并对CuAAC的后期研究工作进行了简要展望。

The most classic“click reaction”is the copper(Ⅰ)-catalyzed[3+2]cycloaddition(CuAAC)of terminal alkynes and organic azides to selectively synthesize 1,4-disubstituted 1,2,3-triazole five-membered heterocyclic compounds.The reaction as a powerful tool was widely used in synthetic chemistry and biochemistry.Based on the potential value of CuAAC,this review summarizes the successful advancement of 1,2,3-triazole-5-copper(Ⅰ),a key intermediate of CuAAC,in the construction of carbon-carbon bonds,including the reaction mechanism and applications of constructing C(sp ^(2))-C(sp ^(3)),C(sp ^(2))-C(sp ^(2))and C(sp ^(2))-C(sp)bonds by using this intermediate,and gives a brief prospect of the future research work of CuAAC.