| Synthesis of difluoromethylated benzylborons via rhodium(Ⅰ)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes |
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| 作者姓名： | Yuanhong Cai Donghang Tan Qiqi Zhang Wenxin Lv Qingjiang Li Honggen Wang |
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| 作者单位： | Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China;; State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China |
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| 基金项目： | Generous financial support from the National Natural Science Foundation of China (No. 21971261), Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery (No. 2019B030301005), Key Project of Chinese National Programs for Fundamental Research and Development (No. 2016YFA0602900), and the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program (No. 2017BT01Y093) is gratefully acknowledged. |
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| 摘 要： | The synthesis of bo rylated orga nofluorines is of great interest due to their potential values as synthons in modular construction of fluorine-containing molecules.Reported herein is a rhodium-catalyzed hydrobo ration of arylgem-difluoroalkenes leading to a series of α-difluoromethylated benzylborons.The use of cationic rhodium catalyst and a biphosphine ligand with large bite angle was crucial for reactivity by offering good regioselectivity and diminishing the undesired β-F elimination.Preliminary derivatizations of the products were conducted to showcase the utility of this protocol.
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| 关 键 词： | RHODIUM HYDROBORATION Difluoromethy gem-Difluoroalkene β-F elimination |
| 收稿时间： | 9 February 2020 |
Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes |
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| Yuanhong Cai,Donghang Tan,Qiqi Zhang,Wenxin Lv,Qingjiang Li,Honggen Wang.Synthesis of difluoromethylated benzylborons via rhodium(I)-catalyzed fluorine-retainable hydroboration of gem-difluoroalkenes[J].Chinese Chemical Letters,2021,32(1):417-420. |
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| Authors: | Yuanhong Cai Donghang Tan Qiqi Zhang Wenxin Lv Qingjiang Li Honggen Wang |
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| Institution: | Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China; State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China |
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| Abstract: | The synthesis of borylated organofluorines is of great interest due to their potential values as synthons in modular construction of fluorine-containing molecules. Reported herein is a rhodium-catalyzed hydroboration of aryl gem-difluoroalkenes leading to a series of α-difluoromethylated benzylborons. The use of cationic rhodium catalyst and a biphosphine ligand with large bite angle was crucial for reactivity by offering good regioselectivity and diminishing the undesired β-F elimination. Preliminary derivatizations of the products were conducted to showcase the utility of this protocol. |
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| Keywords: | Rhodium Hydroboration Difluoromethy gem-Difluoroalkene β-F elimination |
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