School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian, 116024, P. R. China.
State Key Laboratory of Fine Chemicals, Dalian University of Technology , Dalian, 116024, P. R. China.
Org Lett. 2017 Nov 17;19(22):6200-6203. doi: 10.1021/acs.orglett.7b03123. Epub 2017 Nov 7.
A highly regioselective method to access 5-amido fully substituted 1,2,3-triazoles by iridium-catalyzed azide-ynamide cycloaddition under mild, air, aqueous, and bioorthogonal conditions is reported. The excellent regioselectivities may derive from the strong coordination between the carbonyl oxygen of ynamide and the π-acidic iridium. Since the iridium ion is insensitive to oxygen/water and exhibits low cytotoxicity, it could catalyze this reaction in both organic and biological environments efficiently. Preparation in gram-scale and application in carbohydrates highlight this method.
报道了一种在温和、有氧、水相和生物正交条件下，通过铱催化叠氮化物-炔酰胺环加成反应高区域选择性地合成 5-酰胺完全取代的 1,2,3-三唑的方法。优异的区域选择性可能源于炔酰胺羰基氧与π-酸铱的强配位。由于铱离子对氧/水不敏感且细胞毒性低，它可以在有机和生物环境中高效催化该反应。克级制备和在碳水化合物中的应用突出了该方法的优势。
