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Carbon-carbon Coupling Reactions Catalyzed By MCM-41-supported Bidentate Nitrogen Palladium (Ⅱ)

Posted on:2012-06-08Degree:MasterType:Thesis
Country:ChinaCandidate:L YinFull Text:PDF
GTID:2211330338968339Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
An MCM-41-supported bidentate nitrogen palladium(Ⅱ) complex [MCM-41- 2N-Pd(OAc)2] was prepared from 3-(2-aminoethylamino)propyltrimethoxysilane via immobilization on MCM-41, followed by reacting with palladium acetate.In order to evaluate the catalytic activity of MCM-41-2N-Pd(OAc)2, we studied cross-coupling reaction of acyl chlorides and terminal alkynes catalyzed by MCM-41-2N-Pd(OAc)2 for the formation of ynones. The results showed that reactions proceeded very smoothly in the presence of a catalytic of MCM-41-2N-Pd(OAc)2 and CuI, giving the corresponding coupled products in good to high yields. This novel supported palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.We also studied tandem cross-coupling/condensation reaction of acyl chlorides, terminal alkynes and hydrazine catalyzed by MCM-41-2N-Pd(OAc)2, providing a novel one-pot method for the preparation of pyrazoles. It was founded that the MCM-41-2N-Pd(OAc)2 exhibits high catalytic activity in both the reaction of acyl chlorides with arylbismuths and the reaction of aryl iodides with arylbismuths, giving the corresponding coupled products in good to high yields, providing a green procedure for the synthesis of diaryl ketones and biaryls, respectively. The novel supported bidentate nitrogen palladium catalyst can be easily recovered by simple filtration and reused many times without loss of activity.
Keywords/Search Tags:MCM-41-supported bidentate nitrogen palladium(Ⅱ), cross-coupling, ynone, pyrazole, diaryl ketone, biaryl
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