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Palladium-catalyzed Tandem Cyclization Heteroarylation Of Chloride-trifluoropropene Derivatives And ?-C Elimination Cross-coupling Reaction Involving Oxime Ester

Posted on:2020-03-08Degree:MasterType:Thesis
Country:ChinaCandidate:T ZhangFull Text:PDF
GTID:2381330578959016Subject:Chemistry
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Both indene and indole are important structural units in biologically active compounds.They are also widely present in drug molecules,natural products,and functional materials,and the indene can also be used as a ligand.The ?-C elimination strategy is also widely used in organic synthesis.Particularly,the metal complex formed via ?-C elimination can be used as a nucleophilic reagent for a series of coupling reactions.The acetylene compounds are not only widely found in natural products,but also have an important role in organic synthesis.In this paper,the synthesis of compounds containing both indene and indole structural units and the cross-coupling reaction of metal complexes formed via ?-C elimination were studied.The main contents of this paper are as follows:(1)The recent advances of the synthesis of indene derivatives,and the application of?-C elimination strategies in C-C activation reactions.(2)A transitin-metal-free C-N bond forming reaction of chloride-trifluoropropene with nitrogen-containing heterocycle has been developed,which is suitable for nitrogen-containing heterocycles such as hydrazine,pyrrole and pyrazole.The resulting 1,5-enyne can be used to further react to construct a larger cyclic compound.(3)The synthesis of trifluoromethylindenylmethyleneindole derivatives via palladium-catalyzed tandem carbocyclization and heteroarylation has been developed.This method can be used of the synthesis of some molecules containing both indene and indole structural units,as well as pyrrole,which provides an efficient method for the development of new drugs.(4)The palladium-catalyzed C-C activation of oxime ester has been developed via oxidative addition,?-C elimination,transmetalation and reduction elimination process.The reaction successfully achieves the functional group conversion between the carbonyl group and the carbon-carbon bond,which provides an efficient method for the synthesis and modification of drug molecules.
Keywords/Search Tags:palladium-catalyzed, heteroarylation, ?-C elimination, C-C activation, indenes
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