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Studies On The Formation Of C-N, C-S Bonds In The Presence Of Peroxide

Posted on:2017-05-07Degree:MasterType:Thesis
Country:ChinaCandidate:J ChenFull Text:PDF
GTID:2271330488960117Subject:Chemistry
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Heteroatomic compounds are an important structural motif in either biologically and pharmaceutically active products or organic materials. Their importance has stimulated considerable interest from organic chemists, and has encouraged the development of many synthetic strategies to prepare these compounds. However, the methods mainly depend on traditional metal-catalyzed cross-couplings. The sustainable and environmentally benign approach for the construction of carbon-heteroatom bonds still needs more studies. In this paper, from the perspective of green environmental protection, we have designed the formation of C-N, C-S bonds in the presence of peroxide.In the first chapter, progress of the formation of carbon-heteroatom bonds in the presence of peroxide has been introduced.In the second chapter, an effective method for the synthesis of methylenebisamides has been developed via the reaction of amides with N,N-dimethylacetamide(DMAC) using Na2S2O8 as the oxidant and(NH42Ce(NO36 as the catalyst in water. The structures of products were identified by 1H NMR,13 C NMR and HRMS. The methodology will provide new strategies for the synthesis of methylenebisamides, which has the advantage of environment- friendly, simple workup and high yield.In the third chapter, We have developed a practical example of metal- free iodine-promoted decarboxyltive couplings between cinnamic acids and sodium benzene sulfinates, which represents an effective synthesis of vinyl sulfones via C–S bond formation reaction. The corresponding products were produced in moderate to good yields under mild reaction conditions using tert-butyl hydroperoxide as the green terminal oxidant.In the fourth chapter, AlC l3-promoted thiolation of acyl C–H bonds with arylsulfonyl hydrazides was developed, which represents an effective synthesis of S-aryl thiocarbamates via C-S bond formation reaction. This protocol features high efficiency, wide functional group tolerance, reliable and less expensive arylsulfonyl hydrazides as starting materials and transition-metal- free conditions. The structures of desired products were confirmed by 1H NMR,13 C NMR and HRMS. The structure of 9l was confirmed by X-ray single crystal diffraction analysis.
Keywords/Search Tags:Heteroatomic compounds, carbon-heteroatom bonds, peroxide
PDF Full Text Request
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