Copper-Mediated Oxidative Radical Addition/Cyclization Cascade: Synthesis of Trifluoromethylated and Sulfonated Quinoline-2,4(1H,3H)-diones
Copper-Mediated Oxidative Radical Addition/Cyclization Cascade: Synthesis of Trifluoromethylated and Sulfonated Quinoline-2,4(1H,3H)-diones
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铜介导的氧化自由基加成/环化级联：三氟甲基化和磺化喹啉-2,4(1H,3H)-二酮的合成
DOI：
10.1002/adsc.201600693
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发表时间：
2016-11-17
影响因子：
5.4
通讯作者：
Li, Ya-Min
中科院分区：
文献类型：
--
作者：
Fu, Hong;Wang, Shi-Sheng;Li, Ya-Min
已经实现了邻氰基芳基丙烯酰胺与三氟甲磺酸钠（朗格卢瓦试剂）的铜介导的氧化自由基加成/环化级联。该反应通过自由基加成、环化和亚胺水解进行，其中环化是通过碳自由基与腈的分子内加成完成的。该转化表现出广泛的底物范围和良好的官能团耐受性，从而为多种三氟甲基化喹啉-2,4(1H,3H)-二酮提供了高效且实用的途径。此外，使用其他亚磺酸钠盐作为磺酰化剂，也通过类似的自由基级联反应得到磺化喹啉二酮。
A copper-mediated oxidative radical addition/cyclization cascade of o-cyanoarylacrylamides with sodium trifluoromethanesulfonate (Langlois' reagent) has been achieved. The reaction proceeds through radical addition, cyclization, and imine hydrolysis, in which the cyclization was accomplished by an intramolecular addition of the carbon radical to the nitrile. This transformation exhibits a wide substrate scope and good functional group tolerance, thus providing a highly efficient and practical access to a variety of trifluoromethylated quinoline-2,4(1H,3H)-diones. Furthermore, using other sulfinic acid sodium salts as sulfonylating agents, sulfonated quinolinediones were also obtained through a similar radical cascade.