铜、钯化合物催化三芳胺的合成
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摘要
本论文主要研究铜和钯的化合物催化卤代芳烃和二芳胺偶联合成三芳胺。
在铜化合物催化合成三芳胺的过程中,用容易合成的两种不同类型配体来摸索合成三芳胺的最佳条件。第一类是以一系列伯胺与乙二醛反应合成乙二亚胺类,这十几个乙二亚胺配体中,N,N′-二苄基乙二亚胺活性最高,它与碘化亚铜组合,在甲苯回流、叔丁醇钾存在的条件下,催化碘苯和二苯胺反应得到85%的三苯胺；另一类配体是脒基配体,用N-烷基苯甲酰胺与二氯亚砜反应后,再与伯胺反应,即可得到一系列氮上含有不同取代基的苯甲脒。通过研究发现,其中N-苯基-N′-叔丁基苯甲脒,在铜催化三芳胺的合成中效果最为明显,在甲苯回流、叔丁醇钾存在的条件下,可使碘苯与二苯胺反应得到高达96%收率的三苯胺。并将这一反应体系用于催化碘代芳烃与二芳胺的反应,合成一系列取代三苯胺时也取得了理想的效果,该反应体系活性高,操作方便,可能有应用价值。对脒基配体用于碘化亚铜高效催化合成三芳胺的反应机理进行了解释。
在过渡金属钯催化合成三芳胺的过程中,先用几个易合成的咪唑氯盐与钯化合物络合,催化溴苯与二苯胺的反应进行了试探,然后又用更易合成的芳基水杨醛亚胺与二氯二三苯膦钯组合催化溴代芳烃与二芳胺的反应,合成三芳胺,得到中等以上的收率,为这类简单、易得、稳定的配体用于钯催化偶联反应方面做了一些工作。
This thesis mainly investigated coupling of aryl halides with diarylamine to synthesize triarylamine derivative catalyzed by the complex of copper and palladium.
To the reaction catalyzed by the complex of copper, two different types of ligands were synthesized and used to explore the optimal conditions for the synthesis of the triphenylamine. The first one is ethylenediimine ligands, and tens of these ligands were made by primary amines and glyoxal, and N, N'-dibenzylethylenedi -imine got the best activity:when it was used as ligand, Cul as catalyst, t-BuOK as base, toluene as solvent, 85% of triphenylamine was got from the reaction of iodobenzene with diphenylamine at 120℃. The second one is amidine ligand.This kind of ligand was synthesized from N-alkyl benzamide,which was reacted with thionyl chloride, then with amines. N-phenyl-N'-tert-butyl- benzamidinium showed obviously excited effect in the reaction of triphenylamine catalyzed by copper. when it was used as ligand, Cul as catalyst, t-BuOK as base, toluene as solvent,96% of triphenylamine was got from the reaction of iodobenzene with diphenylamine at 120℃.When this reation system was used to synthesize triphenylamine derivative,good yield also was obtained. this reaction system may be valueable for high activity, easy to operate. The reaction mechanism of synthesis of triphenylamine was explained for the CuI catalyzed with amidine ligand.
To the synthesis reaction of triarylamine,catalyzed by the complex of Palladium, two different types of ligands were synthesized,The first one is imidazolium chloride ligands, which were used to complex with Pd2(dba)3 to explore the optimal conditions for the synthesis reaction of triphenylamine. The second one is N-aryl salicylideneimine ligand, which was used to synthesize the triphenylamines catalyzed by Pd(PPh3)2Cl2 from aryl bromides with diarylamine. And the yield of the reaction is mediate, and some work was done for the Pd catalyst coupling using the facile, stable ligand.
在铜化合物催化合成三芳胺的过程中,用容易合成的两种不同类型配体来摸索合成三芳胺的最佳条件。第一类是以一系列伯胺与乙二醛反应合成乙二亚胺类,这十几个乙二亚胺配体中,N,N′-二苄基乙二亚胺活性最高,它与碘化亚铜组合,在甲苯回流、叔丁醇钾存在的条件下,催化碘苯和二苯胺反应得到85%的三苯胺；另一类配体是脒基配体,用N-烷基苯甲酰胺与二氯亚砜反应后,再与伯胺反应,即可得到一系列氮上含有不同取代基的苯甲脒。通过研究发现,其中N-苯基-N′-叔丁基苯甲脒,在铜催化三芳胺的合成中效果最为明显,在甲苯回流、叔丁醇钾存在的条件下,可使碘苯与二苯胺反应得到高达96%收率的三苯胺。并将这一反应体系用于催化碘代芳烃与二芳胺的反应,合成一系列取代三苯胺时也取得了理想的效果,该反应体系活性高,操作方便,可能有应用价值。对脒基配体用于碘化亚铜高效催化合成三芳胺的反应机理进行了解释。
在过渡金属钯催化合成三芳胺的过程中,先用几个易合成的咪唑氯盐与钯化合物络合,催化溴苯与二苯胺的反应进行了试探,然后又用更易合成的芳基水杨醛亚胺与二氯二三苯膦钯组合催化溴代芳烃与二芳胺的反应,合成三芳胺,得到中等以上的收率,为这类简单、易得、稳定的配体用于钯催化偶联反应方面做了一些工作。
This thesis mainly investigated coupling of aryl halides with diarylamine to synthesize triarylamine derivative catalyzed by the complex of copper and palladium.
To the reaction catalyzed by the complex of copper, two different types of ligands were synthesized and used to explore the optimal conditions for the synthesis of the triphenylamine. The first one is ethylenediimine ligands, and tens of these ligands were made by primary amines and glyoxal, and N, N'-dibenzylethylenedi -imine got the best activity:when it was used as ligand, Cul as catalyst, t-BuOK as base, toluene as solvent, 85% of triphenylamine was got from the reaction of iodobenzene with diphenylamine at 120℃. The second one is amidine ligand.This kind of ligand was synthesized from N-alkyl benzamide,which was reacted with thionyl chloride, then with amines. N-phenyl-N'-tert-butyl- benzamidinium showed obviously excited effect in the reaction of triphenylamine catalyzed by copper. when it was used as ligand, Cul as catalyst, t-BuOK as base, toluene as solvent,96% of triphenylamine was got from the reaction of iodobenzene with diphenylamine at 120℃.When this reation system was used to synthesize triphenylamine derivative,good yield also was obtained. this reaction system may be valueable for high activity, easy to operate. The reaction mechanism of synthesis of triphenylamine was explained for the CuI catalyzed with amidine ligand.
To the synthesis reaction of triarylamine,catalyzed by the complex of Palladium, two different types of ligands were synthesized,The first one is imidazolium chloride ligands, which were used to complex with Pd2(dba)3 to explore the optimal conditions for the synthesis reaction of triphenylamine. The second one is N-aryl salicylideneimine ligand, which was used to synthesize the triphenylamines catalyzed by Pd(PPh3)2Cl2 from aryl bromides with diarylamine. And the yield of the reaction is mediate, and some work was done for the Pd catalyst coupling using the facile, stable ligand.
引文
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