钯催化吲哚与对甲苯磺酰腙的分子内Heck脱芳构化烯基化反应
Palladium-Catalyzed Intramolecular Heck Dearomative Alkenylation of Indoles with -Tosylhydrazones.
作者信息
Duan Shao-Bo, Zhang Hong-Yu, Ma Yue, Zhao Jiquan, Han Ya-Ping, Zhang Yuecheng, Liang Yong-Min
机构信息
School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
出版信息
J Org Chem. 2022 Aug 19;87(16):10917-10927. doi: 10.1021/acs.joc.2c01209. Epub 2022 Aug 10.
An elegant Pd-catalyzed intramolecular Heck dearomative alkenylation of aryl iodides with functionalized -tosylhydrazones proceeded through a sequential dearomative carbopalladation, migratory insertion, and β-hydride elimination in the presence of Pd(CFCOO) (10 mol %), PPh (30 mol %), and CsCO (2.0 equiv) in 1,4-dioxane (2.0 mL) at 120 °C for 14 h under an argon atmosphere. This cascade cycloaddition protocol provided a reliable and versatile approach to a sequence of structurally diverse indolines in moderate to good yields with good functional group compatibility. In addition, the synthetic robustness of the methodology is highlighted by a scaled-up experiment and derivatization of products via epoxidation and reduction reactions.
在氩气氛围下，于120℃在1,4 - 二氧六环（2.0 mL）中，以Pd(CFCOO)（10 mol%）、PPh（30 mol%）和CsCO（2.0当量）存在，芳基碘化物与官能化对甲苯磺酰腙进行了优雅的钯催化分子内Heck脱芳烯基化反应，该反应通过连续的脱芳基碳钯化、迁移插入和β - 氢消除进行。这种串联环加成方案提供了一种可靠且通用的方法，以中等至良好的产率和良好的官能团兼容性合成一系列结构多样的二氢吲哚。此外，放大实验以及通过环氧化和还原反应对产物进行衍生化突出了该方法的合成稳健性。
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