The Research On The Synthesis Of The Substituted Indoles Via Cul-catalyzed Ullmann Coupling In The Tandem Reactions

This thesis studies on CuI-catalyzed tandem reactions involving Ullmann C-Ncoupling, and the reactions of substituted ethyl α-bromo cinnamates with TBAF. Thethesis consists of three chapters. In the first chapter, the synthetic applications ofCuI-catalyzed Ullmann coupling reaction and the related series reaction are brieflyreviewed. The second and the third Chapters describe my own works which aresummarized as follows:(1) The research on the synthesis of the substituted indoles via CuI-catalyzedUllmann coupling in the tandem reactions. The results show that the reaction of3-(2-Amino-phenyl)-2-bromo-acrylic acid ethyl esters with Aryl halides can producesubstituted indoles in the condition of CuI as catalyst, DMEDA as ligand, K2CO3asbase, in Dioxane at110℃.(2) The research on the reaction of substituted ethyl α-bromo cinnamates withTBAF. We found that when ethyl α-bromo cinnamates was2-substituted. the resultswas elimination product. However, incorporating a substituent at para-or meta-position of the phenyl ring reacted in the same way, the results was giving rise to thecorresponding fluorination product.