Copper-Catalyzed Coupling Reaction Of CF₃CH₂OH With Arylboronic Acids And Synthesis Of 3-Pyridyl Azetidine Derivatives

In the thesis, an efficient copper-catalyzed Chan-Lam reaction of trifluoroethanol with aryl boronic acids has been researched. The synthesis of 3-pyridyl azetidine derivatives was also investigated.1. The coupling reaction of trifluoroethanol with aryl boronic acidsAn efficient copper-catalyzed coupling reaction of trifluoroethanol with a variety of aryl- and heteroaryl boronic acids has been developed. This research provided a practical method to synthesize trifluoroethyl aryl ethers under mild conditions in moderate to good yields. The result showed that the combination of Cu(OAc)2·H2O as catalyst, DMAP as the base and ligand, and trifluoroethanol as one of the reactant and solvent is optimum condition. Under the optimum conditions, the aryl boronic acids were reacted with trifluoroethanol at 40 oC for 1h, while heteroaryl boronic acids were treated with trifluoroethanol at 80 oC for 3h to get the desired products. Scheme 1 The reaction of trifluoroethanol with aryl boronic acids2. Synthesis of 3-pyridyl azetidine derivativesA four steps procedure for the synthesis of 3-pyridyl azetidine derivatives was designed and improved based on previous reports. A series of 3-pyridyl azetidine derivatives were prepared using azetidin-3-ol hydrochloride as starting material.Scheme 2 The synthesis of 3-pyridyl azetidine derivatives...