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Synthesis of Triphenylamine Derivatives Catalyzed by Copper, Palladium Compounds

Author: LiuJing
Tutor: TaoXiaoChun
School: East China University of Science and Technology
Course: Organic Chemistry
Keywords: triphenylamine Post-Ullmann reactions Buchwald-Hartwig reaction
CLC: TQ246.31
Type: Master's thesis
Year: 2011
Downloads: 182
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Abstract


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.

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CLC: > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of aromatic compounds > Aromatic nitrogen compounds > Aromatic amines and their derivatives > Aromatic amines
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