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Palladium-catalyzed Tetravnes To Construct Yne-functionalized Anilines/Aryl Halides Through Domino Cvclization

Posted on:2014-12-07Degree:MasterType:Thesis
Country:ChinaCandidate:H ZhangFull Text:PDF
GTID:2251330425452067Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
1. Palladium-catalyzed Tetraynes build the alkyne functionalizedaromatic amine reaction.Domino rings having various substituents (-Cl,-F,-CH3,-OCH3) tetraynesderivatives occurs with an organic amine (primary amine, secondaryamine, tertiary amine) palladium-catalyzedreactions, the formation of27-aryl amine product. This type of Domino cyclizing reaction conditionswere optimized, and palladium acetate is a relatively good catalyst, thereaction is carried out at about90°C to100°C, more appropriate. Theelectronic effects of the substituents have a certain impact on the yield ofthe product. In this reaction, the temperature is also a critical condition,when the reaction temperature below80°C the reaction is difficult tooccur when the reaction temperature is higher than130°C, the finalproduct can not be separated. Means of IR, NMR, mass spectrometry andUV compound structures were determined, and the structure of thecompound in a single-crystal X-ray structure analysis.2.Palladium-catalyzed Tetraynes build alkyne functional groupreactions of aryl halides.Palladium-catalyzed tetraynes derivatives having various substituents(-Cl,-F,-CH3,-OCH3) with a halogenated allyl (allyl chloride, allylbromide, allyliodine) occurs Domino is the cyclization reaction generates25aryl halides product and five stripped the aryl halides product onecarboxyl group. This type of Domino cyclizing reaction conditions wereoptimized, and palladium acetate is a relatively good catalyst, the reactionis carried out at about90°C to100°C, more appropriate. The electroniceffects of the substituents have a certain impact on the yield of the product. In this reaction, the temperature is also a critical condition, whenthe reaction temperature below80°C the reaction is difficult to occurwhen the reaction temperature is higher than130°C, the final productcan not be separated. The obtained compound with a structureidentification means such as infrared, NMR, MS and UV, and3whereinthe compound structure is also the X-ray crystal structure analysis.
Keywords/Search Tags:Palladium-catalyzed, Tetraynes, Aryl halides, Anilines, theCH activation, Cyclization, Domino reaction
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