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The Perfluorophenylation Of Disulfides And 3-iodine-2-arylbenzofuran

Posted on:2019-12-16Degree:MasterType:Thesis
Country:ChinaCandidate:Z J LiuFull Text:PDF
GTID:2371330548482313Subject:Chemistry
Abstract/Summary:
Fluorinated organic compounds are widely applied in various fields,such as medicine and material.Therefore,fluorine chemistry has always been one of the most important field in chemistry.The method of fluorine containing block can be used for the synthesis of fluorinated compounds.Generally,this method does not involve the cutting and construction of C-F bonds.The reaction conditions are relatively mild and the selectivity of reaction is relatively good.These advantages above have brought a lot of convenience to the synthesis of organic fluorine compounds,thus attracted the attention of many chemists.Based on previous research,the authors explored the synthesis methodology of 2,3,5,6-tetrafluorobenzene sulfides and 3-(perfluorophenyl)-2-arylbenzofuran compounds with pentafluorobenzene as the source of perfluorophenyl group.1)A new method for the synthesis of 2,3,5,6-tetrafluorobenzene sulfides based on disulfides and pentafluobenzene had been developed.This transition-metal-free reaction requires mild reaction conditions and simple operation,which is in accordance with the concept of environmentfriendly chemical research.In this paper,the substrate ratio,base and solvent were optimized.The optimal reaction conditions were released.The scope of the reaction was studied under the optimal reaction conditions,and a series of 2,3,5,6-tetrafluorophenyl dialkyl thioether and 2,3,5,6-etrafluorophenyl diaryl thioether compounds were synthesized.The mechanism of the reaction was proposed based on a series of experiments.2)A new method for the synthesis of 3-perfluorophenyl-2-arylbenzofuran using pentafluobenzene as perfluorophenyl source had been developed.The authors have studied the synthesis of 3-perfluorophenyl-2-phenylbenzofuran by using pentafluobenzene and pentafluorophenyltrimethylsilane as perfluorophenyl source respectively.The reaction conditions such as catalysts,ligands,additives,solvents and reaction temperatures were optimized and the optimal reaction conditions were explored.Under the optimal reaction conditions,substrates scope was expanded.A series of 3-perfluorophenyl-2-arylbenzofuran compounds were synthesized in good yields.The feasibility of synthesizing 3-perfluorophenyl-2-phenylbenzofuran by one pot method is verified,and the factors affecting the one pot method were also studied.
Keywords/Search Tags:perfluorophenylation, organic fluoride, pentafluobenzene, fluorinated thioether, fluorinated benzofuran derivatives
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