Study On The Electrophilic Cyclization Of Alkyne And The Cycloaddition Of Benzyne

Electrophilic cyclization of alkyne and cycloaddition based on alkyne are hot research fileds in organic synthetic chemistry, and these reactions had been widely applied in designing and synthesizing the functional organic molecules, such as optoelectronics molecules and bioactive molecules. In this thesis, iodine-mediated electrophilic cyclizations of alkyne as well as the cascade reactions based on aryne intermediates are reviewed. The details of this thesis are listed as follows:1.2,3-Diiodoindenes were synthesised via iodine-mediated electrophilic cyclizations of propargylic alcohols. After the screening of the reaction conditions and the investigation of the substrate scope, a series of2,3-diiodoindenes were efficiently obtained in good yeilds. Moreover, these2,3-diiodoindenes could be easily extended to13H-indeno[1,2-l]phenanthrenes via a sequential of Suzuki cross-coupling and Scholl oxidation. After theoretical calculating and experimental examination of2,3-diarylindenes and13H-indeno[1,2-l]phenanthrenes, it was noticed that13H-indeno[1,2-l]phenanthrenes possessed the potential to be applied as the blue emitters in OLED.(see Section2, Chapter2in this thesis)2. Benzyne was realized as one of the key intermediates in organic synthesis and had been widely used. By testing the reaction between aryne and aroyl cyanide in N,N-dimethylformamide solution, a-amino-a-aryl carbonitrile was obtained and its structure was confirmed by single crystal analysis. DMF was indicated to participate the reaction. By investigating the reaction conditions and the substrate scope, it was noticed that this method might be used in the construction of a-amino-a-aryl carbonitriles for the discovery of bioactive molecules.(see Section3, Chapter2in this thesis)...