环加成
区域选择性
炔烃
三氮烯
组合化学
化学
分子间力
表面改性
催化作用
有机化学
分子
物理化学
作者
Shuaipeng Lv,Hui Zhou,Xin Yu,Yilin Xu,Huihui Zhu,Min Wang,Haitao Liu,Zhicheng Dai,Guibo Sun,Xue Gong,Lei Wang
标识
DOI:10.1038/s42004-019-0168-6
摘要
Abstract 3-Trifluoromethylpyrazole and its derivatives are of major interest to both the agrochemical and pharmaceutical industry for their diverse biological activities. Reported routes for the synthesis of 3-trifluoromethylpyrazoles are hindered by poor regioselectivity and limited scope of application. Here we report a directed Lewis base catalyzed intermolecular triazene-alkyne cycloaddition. It is featured that the combination of 1,8-diazabicyclo[5.4.0]undec-7-ene and 2,2,2-trifluorodiazoethane produces reactive triazene intermediates, which readily participate in cycloaddition reactions with terminal/internal alkynes, thus assembling densely substituted 3-trifluoromethylpyrazole scaffolds with environmental friendliness and operational simplicity. Synthetic utility of the protocol is highlighted by late-stage functionalization and scaffolds diversification. The practical value is also emphasized in potential platelet aggregation inhibitor synthesis.
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