Fletcher James T, Reilly Jacquelline E
Department of Chemistry, Creighton University, 2500 California Plaza, Omaha, NE 68178, USA.
Tetrahedron Lett. 2011 Oct 19;52(42):5512-5515. doi: 10.1016/j.tetlet.2011.08.069.
This study examined whether commercially available diazonium salts could be used as efficient aromatic azide precursors in one-pot multi-step click transformations. Seven different diazonium salts, including Fast Red RC, Fast Blue B, Fast Corinth V and Variamine Blue B were surveyed under aqueous click reaction conditions of CuSO(4)/Na ascorbate catalyst with 1:1 t-BuOH:H(2)O solvent. Two-step tandem reactions with terminal alkyne and diyne co-reactants led to 1,2,3-triazole products in 66%-88% yields, while three-step tandem reactions with trimethylsilyl-protected alkyne and diyne co-reactants led to 1,2,3-triazole products in 61%-78% yields.
本研究考察了市售重氮盐是否可用作一锅多步点击转化中高效的芳基叠氮化物前体。在硫酸铜/抗坏血酸钠催化剂、叔丁醇与水体积比为1:1的溶剂的水相点击反应条件下，对七种不同的重氮盐进行了研究，包括固红RC、固蓝B、固柯林斯V和变胺蓝B。与末端炔烃和二炔共反应物进行的两步串联反应，生成1,2,3-三唑产物的产率为66%-88%，而与三甲基硅基保护的炔烃和二炔共反应物进行的三步串联反应，生成1,2,3-三唑产物的产率为61%-78%。
