串联的铜、钯催化偶联-环化合成二芳胺基芴

doi:10.6023/cjoc201503041

有机化学 ›› 2015, Vol. 35 ›› Issue (8): 1682-1690.DOI: 10.6023/cjoc201503041 上一篇下一篇

研究论文

串联的铜、钯催化偶联-环化合成二芳胺基芴

蔡良珍, 蔺卉, 刘涛平, 陶晓春

华东理工大学化学与分子工程学院上海 200237

收稿日期:2015-03-26 修回日期:2015-04-14 发布日期:2015-04-27
通讯作者: 陶晓春 E-mail:xctao@ecust.edu.cn
基金资助:
高等学校博士学科点专项科研基金(No. 20120074120008)和上海市分子催化和功能材料重点实验室(复旦大学, No. 201MCIMKF01)资助项目.

Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions

Cai Liangzhen, Lin Hui, Liu Taoping, Tao Xiaochun

School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237

Received:2015-03-26 Revised:2015-04-14 Published:2015-04-27
Supported by:
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).

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摘要/Abstract

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.

关键词: 二芳胺基芴, C—H活化, 铜催化, 钯催化

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, ¹³C NMR, HRMS, IR and UV-vis.

Key words: diarylaminofluorene, C—H activation, copper-catalyzed, palladium-catalyzed

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蔡良珍, 蔺卉, 刘涛平, 陶晓春. 串联的铜、钯催化偶联-环化合成二芳胺基芴[J]. 有机化学, 2015, 35(8): 1682-1690.

Cai Liangzhen, Lin Hui, Liu Taoping, Tao Xiaochun. Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions[J]. Chin. J. Org. Chem., 2015, 35(8): 1682-1690.

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串联的铜、钯催化偶联-环化合成二芳胺基芴

Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions

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