The Synthesis Of3-Hydroxy-2-Oxindoles And Diaryl Ethers

The thesis comprises five chaptersChapter one mainly summarizes the application of copper-catalyzedcoupling reactions of arylboronic acid in organic synthesis in recentyears. Arylboronic acid has long been a major concern among organicscientific work due to its striking advantages, such as thermal stability,good functional compatibility and resistance to air or water, etc. Amongthem, copper-catalyzed coupling reactions of arylboronic acid developedin recent years attract the attentions of researchers especially as a resultof its low price, low toxicity and high efficiency etc. This thesis will befocused on recent advances in the copper-catalyzed coupling reactions ofarylboronic acid.Chapter two is the review of the synthetic methods of3-hydroxy-2-oxindoles firstly. The copper-catalyzed coupling reaction ofindolin-2,3-ones with arylboronic acids was studied in a systematic way,achieving3-hydroxy-2-oxindoles in good to excellent yields. This present catalytic system shows broad functional group tolerance.Moreover, the rigorous exclusion of air/moisture is not required in thesetransformations.Chapter three describes copper-catalyzed coupling of nitroareneswith arylboronic acids leading to unsymmetrical diaryl ethers inmoderate to excellent yields. Preliminary mechanistic experiments usingdeuterium labeling showed that the oxygen atom was derived from water.The efficiency of this reaction was demonstrated by compatibility with awide range of groups. Moreover, the rigorous exclusion of air/moistureis not required in these transformations. Thus, the present methodrepresents a simple and facile procedure to access unsymmetrical diarylethers.The last chapter introduces the general procedures for synthesis of3-hydroxy-2-oxindoles and unsymmetrical diaryl ethers.