钯催化吲哚的分子内Heck脱芳基-二氟乙烯基化反应。
Palladium-catalyzed intramolecular Heck dearomative -difluorovinylation of indoles.
作者信息
Wang Gang, Li Wenqi, Liu Tianxiang, Zhang Yonghong, Wang Bin, Xue Fei, Jin Weiwei, Ma Caiyan, Xia Yu, Liu Chenjiang
机构信息
Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University Urumqi 830017 P. R. China
出版信息
Chem Sci. 2022 Sep 13;13(39):11594-11599. doi: 10.1039/d2sc03169h. eCollection 2022 Oct 12.
A palladium-catalyzed dearomative reaction of indoles has been developed through a domino Heck/-difluorovinylation sequence. By taking advantage of a difluorocarbene precursor (ClCFCOONa), the palladium difluorocarbene ([Pd][double bond, length as m-dash]CF) species was formed smoothly. Then, a migratory insertion/β-H elimination process enabled access to polycyclic indolines containing 1,1-difluoroethylene units in acceptable yields with a broad substrate scope, which also showed dearomative -difluorovinylation for the first time. Remarkably, the superb diversified transformations allowed the product to install various functional groups.
通过多米诺Heck/二氟乙烯基化序列，开发了一种钯催化的吲哚去芳构化反应。利用二氟卡宾前体（ClCFCOONa），顺利形成了二氟卡宾钯（[Pd]=CF）物种。然后，迁移插入/β-H消除过程能够以可接受的产率和广泛的底物范围获得含有1,1-二氟乙烯单元的多环吲哚啉，这也是首次展示去芳构化二氟乙烯基化反应。值得注意的是，出色的多样化转化使产物能够引入各种官能团。
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