文献类型：期刊文献

中文题名：串联的铜、钯催化偶联-环化合成二芳胺基芴

英文题名：Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions

作者：蔡良珍[1];蔺卉[1];刘涛平[1];陶晓春[1]

机构：[1]华东理工大学化学与分子工程学院,上海200237

年份：2015

卷号：35

期号：8

起止页码：1682

中文期刊名：有机化学

外文期刊名：Chinese Journal of Organic Chemistry

收录：CSTPCD;;Scopus;WOS:【SCI-EXPANDED(收录号:WOS:000361846200010)】；北大核心:【北大核心2014】；CSCD:【CSCD2015_2016】；

基金：Project supported by the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20120074120008) and the Shanghai Key Laboratory of Molecular Catalysts and Innovative Materials (Fudan University, No. 2012MCIMKF01).

语种：中文

中文关键词：二芳胺基芴;C—H活化;铜催化;钯催化

外文关键词：diarylaminofluorene; C—H activation; copper-catalyzed; palladium-catalyzed

摘要：发展了一种由串联的铜、钯金属催化偶联-环化合成二芳胺基芴类衍生物的新方法.取代的碘苯与甲基和溴原子互为邻位的苯胺在铜催化下反应生成溴代甲基三苯胺,然后与邻氯苯基硼酸在钯催化下发生Suzuki偶联反应,最后在NHC-Pd催化下发生C(sp3)—H键活化-环化反应.方便地合成了2位,尤其是3位取代的二芳胺基芴类化合物,且均获得了不错的收率.所有化合物均通过了1H NMR,13C NMR,HRMS,IR,紫外和荧光等手段的表征.对其中两个具有代表性的二芳胺基芴的结构运用二维核磁共振技术进行了解析.
A convenient method of tandem copper and palladium catalyzed coupling-cyclizing reactions has been developed for the preparation of diarylaminofluorenes. Methylbromotriphenylamines prepared by the copper-catalyzed reaction of substituted iodobenzenes and methylbromoanilines, coupled with chlorophenylboronic acid under palladium catalyst to obtain the chlorophenylmethyltriphenylamines（V）. A series of diarylaminofluorenes can be generated in good yields through palladium-catalyzed activation of benzylic C（sp3）—H bond of compound V. It was found that the 2-diarylaminofluorenes or 3-diarylaminofluorenes could be efficiently got. These compounds were characterized by 1H NMR, 13 C NMR, HRMS, IR and UV-vis.