Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis
Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis
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DOI：
10.1021/acs.orglett.8b03849
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发表时间：
2018-12
期刊：
影响因子：
5.2
通讯作者：
D. Zheng;A. Studer
中科院分区：
文献类型：
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作者：
D. Zheng;A. Studer
提出了可见光引发的各种烯烃与全氟烷基碘和喹喔啉-2(1H)-酮的α-全氟烷基-β-杂芳基化反应。这种三组分自由基级联反应可以在温和条件下以中等至优异的产率有效合成一系列含有全氟烷基的喹喔啉-2(1H)-酮衍生物。反应通过酸性氨基自由基进行，该酸性氨基自由基很容易去质子化，得到相应的自由基阴离子，能够作为单电子转移还原剂维持自由基链。因此，整个级联被归类为电子催化过程。
A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated to give the corresponding radical anions able to sustain the radical chain as single electron transfer reducing reagents. Hence, the overall cascade classifies as an electron-catalyzed process.