Iridium-Catalyzed γ-Selective Hydroboration of γ-Substituted Allylic Amides
- Hongliang ZhaoHongliang ZhaoGreen Catalysis Center, College of Chemistry, Henan Advanced Institute of Technology, Zhengzhou University, Zhengzhou 450001, ChinaState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, ChinaMore by Hongliang Zhao
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- Qian GaoQian GaoState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, ChinaMore by Qian Gao
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- Yajuan ZhangYajuan ZhangState Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, ChinaMore by Yajuan Zhang
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- Panke Zhang*Panke Zhang*Email: [email protected]Green Catalysis Center, College of Chemistry, Henan Advanced Institute of Technology, Zhengzhou University, Zhengzhou 450001, ChinaMore by Panke Zhang
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- Senmiao Xu*Senmiao Xu*Email: [email protected]State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Science, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000, ChinaKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, ChinaUniversity of Chinese Academy of Sciences, Beijing 100049, ChinaMore by Senmiao Xu
Abstract
Reported here for the first time is the Ir-catalyzed γ-selective hydroboration of γ-substituted allylic amides under mild reaction conditions. A variety of functional groups could be compatible with reaction conditions, affording γ-branched amides in good yields with ≤97% γ-selectivity. We have also demonstrated that the obtained borylated products could be used in a series of C–O, C–F, C–Br, and C–C bond-forming reactions.
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(29)
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(18)
, 2103-2109. https://doi.org/10.1055/a-2103-9140
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(5)
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(19)
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(21)
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(46)
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trans
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(46)
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(71)
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(10)
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(6)
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