钯催化吲哚的去芳香化双芳基化  

Palladium-catalyzed dearomative diarylation of indole

作　　者：贾义霞[1] 李英龙[1] 刘人荣 JIA Yixia LI Yinglong LIU Renrong(College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China)

机构地区：[1]浙江工业大学化学工程学院,浙江杭州310014

出　　处：《浙江工业大学学报》2017年第4期387-390,共4页Journal of Zhejiang University of Technology

基　　金：国家自然科学基金资助项目(21372202)

摘　　要：以钯为催化剂,三环己基膦为配体,芳基硼酸为芳基化试剂,通过吲哚的分子内Heck/Suzuki串联反应实现了吲哚的双官能团化,为合成结构多样性的吲哚啉衍生物提供了一种高效、快捷的方法.通过简单起始原料出发,高产率、高对映选择性地合成了一系列的含有连续叔碳/季碳中心的吲哚林化合物.并系统地研究了反应的溶剂、碱和配体对反应的影响以及底物中各种给电子或吸电子基团对产物收率的影响.重要的是,通过该反应可以顺利实现克级规模制备,体现了方法的优越性及可靠性.A novel Pd-catalyzed bisfunctionaiization of indoles that proceeds via an intramolecular dearomatization/arylation cascade reaction is developed by employing Pd（OAc）2 as a catalyst, PCy3 as a ligand and phenylboronic acid as an arylative reagent, which provides a straightforward and efficient access to structural diversely indolines. A series of indolines bearing vicinal tertiary and quaternary stereocenters can be obtained in excellent yields and derived from easily available starting materials. A set of solvents, bases and ligands were screened to enhance the yield. The effect of substituents was also examined. Importantly, this protocol was amenable to gram-scale synthesis, showing the practicality of this reaction.

关 键 词：钯催化 吲哚 芳基化 去芳构化 串联反应 

分 类 号：O62[理学—有机化学]