空气下无配体钯催化二苯胺和卤代芳烃的C—N偶联

doi:10.6023/A1202122

化学学报 ›› 2012, Vol. 70 ›› Issue (15): 1655-1659.DOI: 10.6023/A1202122 上一篇下一篇

研究论文

空气下无配体钯催化二苯胺和卤代芳烃的C—N偶联

张斌彬, 詹丹, 张小平, 向沁洁, 曾庆乐

成都理工大学材料与化学化工学院绿色催化合成研究所成都 610059

投稿日期:2012-02-12 发布日期:2012-05-18
通讯作者: 曾庆乐 E-mail:qinglezeng@hotmail.com
基金资助:
项目受四川省国际科技合作与交流研究计划项目(No. 2011HH0016)、成都理工大学优秀创新团队培育计划(No. HY0084)和地质灾害防治与地质环境保护国家重点实验室开放基金(No. SKLGP2012K005)资助.

Ligand-free Pd-Catalyzed C—N Coupling of Diphenylamine and Aryl Halides under Air

Zhang Binbin, Zhan Dan, Zhang Xiaoping, Xiang Qinjie, Zeng Qingle

Institute of Green Catalysis and Synthesis, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059

Received:2012-02-12 Published:2012-05-18
Supported by:
Project supported by the International Sci-tech Cooperation and Exchange Research of Sichuan Province (No. 2011HH0016), Incubation Program for Excellent Innovation Team of Chengdu University of Technology (No. HY0084), Opening Fund of State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (No. SKLGP2012K005).

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摘要/Abstract

研究了空气下无配体Pd(OAc)₂在弱碱碳酸钾存在下催化二苯胺和溴代芳烃的C—N偶联合成三苯胺类化合物. 与传统合成方法相比, 该反应可以在无配体存在下在空气和温和的条件下进行, 即, 无需无水无氧操作条件, 操作特别方便. 催化剂用量、碱、溶剂、反应温度、反应时间等因素对反应的影响均做了考察. 优化的反应条件是: 在Pd(OAc)₂ (3 mol%)和K₂CO₃ (1.5 equiv.)存在下, 二苯胺和溴代芳烃在DMSO中在空气下在90 ℃加热24 h. 溴代芳烃上的吸电子基团和二苯胺上的给电子基团有利于该偶联反应的进行, 其中4-硝基三苯胺的产率高达93%.

关键词: 无配体, 空气, 钯催化, 三苯胺, 4-硝基三苯胺, C—N偶联反应

Triphenylamine derivatives are extensively used as a number of organic dyes, drugs, intermediates, dye-sensitized solar cells (DSSCs) and organic electroluminescence materials. It is valuable to discover a new synthetic method of triphenylamines with mild reaction conditions, easy-operation, and cheap starting materials. During our research of C—H bond activation, accidentally we found palladium acetate accomplished the C—N cross coupling of diphenylamine and 4-nitrobromobenzene under air. This discovery meets one of hot research topics of modern organic chemistry, that is, transition-metal-catalyzed reactions which must operate under inert atmosphere in the traditional procedures now can be performed under air. Consequently, ligand-free Pd(OAc)₂-catalyzed C—N cross coupling of diphenylamines and aryl halides under air for synthesis of triphenylamines was studied in details. The effect of catalyst loading, base, additives, solvents and reaction time on this transformation was investigated. The optimized conditions were as follows: Pd(OAc)₂ (3 mol%), K₂CO₃ (1.5 equiv.), heated at 90 ℃ in DMSO under air. Electron-withdrawing group of phenyl bromides and electron-donating group of diphenylamine benefit the coupling reaction, and among them, 4-nitrotriphenylamine gave yield up to 93%. Compared with traditional methods, the reactions were conducted under air and mild conditions in absence of ligand, that is, anhydrous and oxygen-free conditions are not required, and operation is extremely easy.

Key words: ligand-free, under air, palladium catalysis, triphenylamines, 4-nitrotriphenylamine, C—N cross coupling

引用此文

张斌彬, 詹丹, 张小平, 向沁洁, 曾庆乐. 空气下无配体钯催化二苯胺和卤代芳烃的C—N偶联[J]. 化学学报, 2012, 70(15): 1655-1659.

Zhang Binbin, Zhan Dan, Zhang Xiaoping, Xiang Qinjie, Zeng Qingle. Ligand-free Pd-Catalyzed C—N Coupling of Diphenylamine and Aryl Halides under Air[J]. Acta Chimica Sinica, 2012, 70(15): 1655-1659.

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空气下无配体钯催化二苯胺和卤代芳烃的C—N偶联

Ligand-free Pd-Catalyzed C—N Coupling of Diphenylamine and Aryl Halides under Air

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