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苯基脒/碘化亚铜催化碘代芳烃与二芳胺的反应

Reaction of Aryl Iodides and Diarylamines Catalyzed by Benzamidine/CuI

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【作者】 蔡良珍林智星刘京刘涛平恰格德尔·爱蓉陶晓春

【Author】 CAI Liang-zhen,LIN Zhi-xing,LIU Jing,LIU Tao-ping, CHAGADER Ariun,TAO Xiao-chun(School of Chemistry and Molecular Engineering,East China University of Science and Technology,Shanghai 200237,China)

【机构】 华东理工大学化学与分子工程学院

【摘要】 N-烷(芳)基苯甲酰胺与氯化亚砜作用后,在三乙胺存在下与芳伯胺或脂肪伯胺反应,方便、高产率地得到了6个N,N′-烷基或芳基苯甲脒;然后将其作为配体应用于铜催化的碘苯与二苯胺的偶联反应中,该类配体显示出了良好的活性,其中N-苯基-N′-叔丁基苯甲脒(L6)的活性最高,产率达到96%;不同取代的碘代芳烃和含有吸电子或供电子基团的二苯胺用这一催化体系进行底物扩展,均能以很高的产率得到偶联产物。将这一催化体系应用于OLED(Organic LightEmitting Diode)的空穴传输材料N,N,N′,N′-四苯基联苯二胺(TPB)及其溴代的衍生物的合成中,分别以77%和70%的产率得到目标产物。

【Abstract】 N-alkyl(aryl) benzamide reacted with thionyl chloride,and then in the presence of triarylamine reacted with arylamine or alkylamine.Six of benzamidines were gotten in high yields by this way.These ligands were applied in the reaction of phenyliodide and diphenylamine catalyzed by copper iodide,and N-phenyl-N′-tertbutylbenzamidine(L6) showed the best yield(96%) among these ligands.The scope of the reaction was examined,and various aryliodides and diarylamines with electron-donating and electron-withdrawing groups were reacted under optimized reactions.Most of them got excellent yields.This catalytic system was also used in synthesis of hole-transporting materials TPB of OLED(Organic Light Emitting Diode) and its bromo derivatives and good yields were obtained(77% and 70%,respectively).

【基金】 上海市分子催化和功能材料重点实验室项目(复旦大学,2012MCIMKF01)
  • 【文献出处】 华东理工大学学报(自然科学版) ,Journal of East China University of Science and Technology(Natural Science Edition) , 编辑部邮箱 ,2013年03期
  • 【分类号】O643.32
  • 【被引频次】1
  • 【下载频次】148
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