Planar chiral 2-(trifluoromethyl)quinoline-fused ferrocenes via palladium(0)-catalyzed C-H functionalization of trifluoroacetimidoyl chlorides

被引:25
|
作者
Zhang, An-An [1 ]
Chen, Chao [1 ]
Gao, Yushen [1 ]
Mo, Mingyang [1 ]
Shen, Ren-Zeng [1 ]
Zhang, Yu-Heng [1 ]
Ishida, Naoki [2 ]
Murakami, Masahiro [2 ]
Liu, Lantao [1 ,3 ,4 ]
机构
[1] Shangqiu Normal Univ, Coll Chem & Chem Engn, Henan Engn Lab Green Synth Pharmaceut, Shangqiu 476000, Peoples R China
[2] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[4] Peking Univ, Coll Chem, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
来源
GREEN SYNTHESIS AND CATALYSIS | 2021年 / 2卷 / 03期
基金
中国国家自然科学基金;
关键词
Planar -chiral ferrocenes; Palladium; C -H functionalization; 2-(Trifluoromethyl)quinolines; Trifluoroacetimidoyl chlorides; ENANTIOSELECTIVE SYNTHESIS; BOND FUNCTIONALIZATION; RADICAL TRIFLUOROMETHYLATION; ASYMMETRIC CATALYSIS; COUPLING REACTION; ISOCYANIDES; ARYLATION; LIGANDS; FLUOROALKYLATION; CYCLOADDITION;
D O I
10.1016/j.gresc.2021.05.004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic enantioselective synthesis of planar chiral 2-(trifluoromethyl)quinoline-fused ferrocenes has been achieved through Pd(0)-catalyzed C-H functionalization with trifluoroacetimidoyl chlorides as electrophilics. With commercially available ligand and palladium precursor, the reaction proceeds smoothly generating 2-perfluoroalkylated quinoline-fused ferrocenes in high yields and enantioselectivities.
引用
收藏
页码:311 / 314
页数:4
相关论文
共 50 条
  • [1] Synthesis of planar chiral isoquinolinone-fused ferrocenes through palladium-catalyzed C-H functionalization reaction
    Liu, Lantao
    Liu, Huihui
    Zuo, Zhenzhen
    Zhang, An-An
    Li, Zhongyi
    Meng, Tuanjie
    Wu, Wei
    Hua, Yuanzhao
    Mao, Guoliang
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 239 - 242
  • [2] 2-(Trifluoromethyl)indoles via Pd(0)-Catalyzed C(sp3)-H Functionalization of Trifluoroacetimidoyl Chlorides
    Pedroni, Julia
    Cramer, Nicolai
    ORGANIC LETTERS, 2016, 18 (08) : 1932 - 1935
  • [3] Palladium(0)-Catalyzed Asymmetric C-H Alkenylation for Efficient Synthesis of Planar Chiral Ferrocenes
    Gao, De-Wei
    Gu, Yiting
    Wang, Shao-Bo
    Gu, Qing
    You, Shu-Li
    ORGANOMETALLICS, 2016, 35 (18) : 3227 - 3233
  • [4] Palladium-Catalyzed Asymmetric C-H Arylation for the Synthesis of Planar Chiral Benzothiophene-Fused Ferrocenes
    Xu, Bing-Bin
    Ye, Jie
    Yuan, Yu
    Duan, Wei-Liang
    ACS CATALYSIS, 2018, 8 (12): : 11735 - 11740
  • [5] Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization
    Huang, Jianpian
    Gu, Qing
    You, Shuli
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (01) : 51 - 61
  • [6] Copper/BINOL-Catalyzed Enantioselective C-H Functionalization toward Planar Chiral Ferrocenes Under Mild Conditions
    Zhang, Zhuo-Zhuo
    Zhou, Gang
    Yue, Qiang
    Yao, Qi-Jun
    Shi, Bing-Feng
    ACS CATALYSIS, 2024, 14 (06) : 4030 - 4039
  • [7] Palladium-catalyzed intramolecular C-H bond functionalization of trifluoroacetimidoyl chloride derivatives: Synthesis of 6-trifluoromethyl-phenanthridines
    Zhu, Mei
    Fu, Weijun
    Zou, Guanglong
    Xu, Chen
    Wang, Zhiqiang
    JOURNAL OF FLUORINE CHEMISTRY, 2014, 163 : 23 - 27
  • [8] Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization
    Gao, De-Wei
    Gu, Qing
    Zheng, Chao
    You, Shu-Li
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (02) : 351 - 365
  • [9] Synthesis of planar chiral ferrocenes via a Pd(0)-catalyzed syn-carbopalladation/asymmetric C-H alkenylation process
    Jia, Lixiang
    Liu, Xiaobing
    Zhang, An-An
    Wang, Tao
    Hua, Yuanzhao
    Li, Heng
    Liu, Lantao
    CHEMICAL COMMUNICATIONS, 2020, 56 (11) : 1737 - 1740
  • [10] Enantioselective Access to 1H-Isoindoles with Quaternary Stereogenic Centers by Palladium(0)-Catalyzed C-H Functionalization
    Grosheva, Daria
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (41) : 13644 - 13647