| Palladium(Ⅱ)-Catalyzed Aminotrifluoromethoxylation of Alkenes:Mechanistic Insight into the Effect of N-Protecting Groups |
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| 作者姓名： | Chaohuang Chen Chuanqi Hou Pinhong Chen Guosheng Liu |
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| 作者单位： | State Key Laboratory of Organometallic Chemistry;Shanghai Hongkong Joint Laboratory in Chemical Synthesis |
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| 基金项目： | We are grateful for financial support from the National Natural Science Foundation of China(Nos.21532009,21761142010,21971255,21728201 and 21790330);the Science and Technology Commission of Shanghai Municipality(Nos.17XD1404500,170A1405200 and 17JC1401200);the strategic Priority Re-search Program(No.XDB2000000);the Key Research Pro-gram of Frontier Science(QYZDISSW-SLH055)of the Chinese Academy of Sciences. |
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| 摘 要： | Summary of main observation and conclusion An eficient palladium-atalyzed regioselective 5 exo aminotrifluoromethoxylation of alkenes has been established herein,which provides practical route towards the synthesis of OCF g-containing prrolidines.tert-Butyloxycarbonyl(Boc)as an amino pro-tecting group plays a signifiant role in both the chemo-and regloselectivities.In addition,preliminary mechanistic studies reveal that the amino protect-ing group of substrates and the counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl-Pd(Ⅱ)intermediates.Moreover,the asymmetric 5-exo aminrifluoromethoxylation reaction has also been achieved by introducing a serelallyl bulky pyri-dinyl-oxazoline ligand.
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| 关 键 词： | PALLADIUM PALLADIUM herein |
Palladium(II)‐Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N‐Protecting Groups |
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| Chaohuang Chen,Chuanqi Hou,Pinhong Chen,Guosheng Liu.Palladium(II)‐Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N‐Protecting Groups[J].Chinese Journal of Chemistry,2020,38(4):346-350. |
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| Authors: | Chaohuang Chen Chuanqi Hou Pinhong Chen Guosheng Liu |
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| Abstract: | An efficient palladium‐catalyzed regioselective 5‐exo aminotrifluoromethoxylation of alkenes has been established herein, which provides a practical route towards the synthesis of OCF3‐containing pyrrolidines. tert‐Butyloxycarbonyl (Boc) as an amino protecting group plays a significant role in both the chemo‐ and regioselectivities. In addition, preliminary mechanistic studies reveal that the amino protecting group of substrates and the counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl‐ Pd(II) intermediates. Moreover, the asymmetric 5‐exo aminotrifluoromethoxylation reaction has also been achieved by introducing a sterically bulky pyridinyl‐oxazoline ligand. |
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| Keywords: | Palladium Alkene Amination Trifluoromethoxylation OCF3– containing Pyrrolidine |
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