Nickel-Catalyzed Azide-Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
Nickel-Catalyzed Azide-Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
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DOI：
10.1021/jacs.7b06338
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发表时间：
2017-09-06
影响因子：
15
通讯作者：
Hong, Sung You
中科院分区：
文献类型：
--
作者：
Kim, Woo Gyum;Kang, Mi Eun;Hong, Sung You
过渡金属催化或无金属叠氮炔环加成是获得 1,4 或 1,5-二取代的 1,2,3-三唑的方法。尽管铜催化环加成反应获得 1,4-二取代产物已应用于生物分子反应系统，但由于底物范围有限或对湿气/空气敏感的催化剂，在水性和环境条件下叠氮炔环加成反应获得互补的 1,5-区域异构体仍然是一个挑战。在此，我们报告了一种使用 Cp2Ni/Xantphos 催化系统获取 1,5-二取代 1,2,3-三唑的方法。该反应在室温下在水和有机溶剂中进行。该协议简单且可扩展，底物范围广泛，包括脂肪族和芳香族底物。此外，通过这种环加成反应可以制备与碳水化合物或氨基酸连接的三唑。
Transition-metal-catalyzed or metal-free azide alkyne cycloadditions are methods to access 1,4 or 1,5-disubstituted 1,2,3-triazoles. Although the copper catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.