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Studies On The Sonogashira Coupling Reaction Catalyzed By Copper-free

Posted on:2010-09-18Degree:MasterType:Thesis
Country:ChinaCandidate:C L LiFull Text:PDF
GTID:2121360275496111Subject:Organic Chemistry
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This thesis mainly consists of three parts:The first part is reviews which contains three chapters.The first chapter introduces the applications and the development of ferrocene and its derivatives.The second chapter summarizes the wide application of coupling reaction catalyzed by Palladium in the confirmation of C-C bond.The coupling reaction involving Sonogashira Coupling reaction,Kumada Coupling raction,Negishi coupling reaction,Hiyama Coupling reaction,Heck Coupling reaction,Suzuki Coupling reaction and Still reaction Coupling.The second part is our study on the synthesis of ferrocenylethynyl aryl ketones via Palladium-Catalyzed Sonogashira carbonylation coupling reaction.Aryl iodides with ferrocenylethyne catalyzed by PdCl2 were carried out using sodium dodecyl sulphonate(SDS) as surfactant and water as solvent.The reaction gave much better yields of aryl ferrocenyethynyl ketones,which proceeded for 6 hours at room temperature under a balloon pressure of carbon monoxide with Et3N as base.All those mentioned compounds have been detennined by 1H NMR,13C NMR,MS,FAB and IR.The third part is our study on the synthesis of 1-ferrocenyl-2-aryl(heteroaryl)-acetylenes via Palladium-Catalyzed Sonogashira coupling reaction.The reaction was performed in short time and in good yield using aryl iodides with ferrocenylethyne as the starting materials,[Pd(dba)2](dba=dibenzylideneacetone) as catalyst,t-BuOK as base,DMF-H2O(v/v=4:1) as solvent at 80℃for 1 hour under a ballon pressure of argon.All those mentioned compounds have been determined by 1H NMR,13C NMR, MS,FAB and IR.
Keywords/Search Tags:Sonogashira
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