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

doi:10.6023/cjoc201503041

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1682-1690.DOI: 10.6023/cjoc201503041 Previous Articles Next Articles

ARTICLE

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).

1. Synthesis of Diarylaminofluorenes through Tandem Copper and Palladium Catalyzed Coupling-Cyclizing Reactions.PDF(2964KB)

Abstract

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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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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