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Copper Catalyzed Coupling Reaction Of Vinylogy Thioester With Amines

Posted on:2014-07-29Degree:MasterType:Thesis
Country:ChinaCandidate:L L WangFull Text:PDF
GTID:2251330401481773Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The formation method of C-N bond is an important area of modern synthetic organicchemistry. Some compounds can be prepared by the synthesis of C-N bond such as amines,amides, nitrogen-containing and so on. Because these compounds have an important role inthe ifeld of organic synthetic, so the synthesis of C-N bond is particularly important. Itssynthesis method has been extensively studied in the ifeld of organic synthetic chemistry.In recent years, our group has been engaged in the a-oxo ketene dithioacetals chemistryresearch, and synthesized a series of ketene dithioacetals compounds. The a-oxo ketenedithioacetals of the double-carbonyl group have the electron-withdrawing effect of thecarbonyl group and the electron-pushing effect of the alkylthio. Based on the features of thea-oxo ketene dithioacetal, electronic cloud density of a-C is high, can be used as anucleophilic center reaction,[5-C as an electrophilic center of reaction. This structure makes itextremely easy take nucleophilic addition elimination reaction with amine, formation of C-Nbond. However, the a-oxo ketene dithioacetals of a single-carbonyl group need strong baseparticipate such as LDA to occur these reactions.In this thesis, the greatest success is the synthesis C-N bond. The method is that thea-oxo ketene dithioacetals of a single-carbonyl group occured coupling reaction with aminesunder the contion of transition metal copper as catalyst and mild temperatures. This methodnot only out of the limitations of the a-oxo ketene dithioacetals of a single-carbonyl groupneeding strong base participation to occur these reaction, but also provided another method ofsynthesis C-N bond.
Keywords/Search Tags:vinylogy thioester, amine, Cu catalyst, coupling reaction
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