Scope and regioselectivity of the 1,3-dipolar cycloaddition of azides with methyl 2-perfluoroalkynoates for an easy,metal-free route to perfluoroalkylated 1,2,3-triazoles |
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| Authors: | Jiamei Wei Jie Chen Jiechao Xu Long Cao Hongmei Deng Weihua Sheng Hui Zhang Weiguo Cao |
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| Affiliation: | 1. Department of Chemistry, Shanghai University, Shanghai 200444, China;2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;3. Key Laboratory of Organofluorine Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;4. Laboratory for Microstructures, Shanghai University, Shanghai 200444, China;5. Shanghai Institute of Space Propulsion, Shanghai 200233, China |
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| Abstract: | 1,3-Dipolar cycloadditions of methyl 2-perfluoroalkynoates with various azides have been examined, leading to a simple metal-free synthetic protocol for the synthesis of perfluoroalkylated 1,2,3-triazoles. The regiochemical results demonstrated that the cycloaddition was controlled by FMO (the frontier molecular obitals) interaction and steric hindrance in transition states. |
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