Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF3-Containing Heterocyclic Compounds

被引：30
|
作者：
Han, Hong Sik [1 ,2 ]
Oh, Eun Hye [2 ,3 ]
Jung, Young-Sik [1 ,2 ]
Han, Soo Bong [1 ,2 ]
机构：
[1] Univ Sci & Technol, Dept Med & Pharmaceut Chem, 217 Gajeongro, Yuseong 34113, Daejeon, South Korea
[2] Korea Res Inst Chem Technol, Div Bio & Drug Discovery, 141 Gajeongro, Yuseong 34114, Daejeon, South Korea
[3] Korea Univ, Dept Chem, 145 Anam Ro, Seoul 02841, South Korea
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 07期
关键词：
ASYMMETRIC HYDROGENATION; FACILE ACCESS; LIGHT; DERIVATIVES; ALKYNES; DESIGN; HETEROARENES; CONSTRUCT; FLUORINE;
D O I：
10.1021/acs.orglett.8b00648
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general photoredox-catalyzed intramolecular cyclization was developed for the synthesis of trifluoromethylated heterocydic compounds. The reaction proceeded smoothly under mild photocatalytic conditions with high functional group tolerance, allowing the preparation of oxygen-, sulfur-, or nitrogen-containing heterocycles of different sizes. The broad.,substrate scope demonstrated the complexity-building potential of the strategy.
引用
收藏
页码：1698 / 1702
页数：5
相关论文
共 50 条
  • [41] Copper-Catalyzed Intermolecular Trifluoromethylazidation of Alkenes: Convenient Access to CF3-Containing Alkyl Azides
    Wang, Fei
    Qi, Xiaoxu
    Liang, Zhaoli
    Chen, Pinhong
    Liu, Guosheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) : 1881 - 1886
  • [42] Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones
    Zhang, Zuxiao
    Tang, Xiao-Jun
    Dolbier, William R., Jr.
    ORGANIC LETTERS, 2016, 18 (05) : 1048 - 1051
  • [43] Synthesis of CF3-containing tetrapeptide surrogates via Ugi reaction/dipolar cycloaddition sequence
    Vorobyeva, Daria V.
    Sokolova, Nadezhda V.
    Nenajdenko, Valentine G.
    Peregudov, Alexander S.
    Osipov, Sergey N.
    TETRAHEDRON, 2012, 68 (03) : 872 - 877
  • [44] Visible-Light Photoredox-Catalyzed Decarboxylative Double Difluoromethylation of β,γ-Unsaturated Carboxylic Acids for the Synthesis of Difluoromethylated Allylic Compounds
    Yao, Zhen
    Li, Gang
    Zhou, Ying
    Xu, Lijin
    Xue, Dong
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (02) : 224 - 229
  • [45] Phosphine-Catalyzed Divergent [4+3] Domino Annulations of CF3-Containing Imines with MBH Carbonates: Construction of Perfluoroalkylated Benzazepines
    Chen, Junlong
    Yin, Zhongmo
    Huang, You
    ORGANIC LETTERS, 2019, 21 (17) : 7060 - 7064
  • [46] Photoredox-catalyzed cascade addition/cyclization of N-propargyl aromatic amines: access to 3-difluoroacetylated or 3-fluoroacetylated quinolines
    Deng, Qinfei
    Xu, Yan
    Liu, Ping
    Tan, Liping
    Sun, Peipei
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01): : 19 - 23
  • [47] Pd-Catalyzed Allylic Alkylation of CF3-Containing Esters with Three Electron-Withdrawing Groups
    Li, Lun
    Huang, Donghui
    Chen, Qing-Yun
    Guo, Yong
    SYNLETT, 2013, 24 (05) : 611 - 614
  • [48] Synthesis of CF3-containing α-alkynyl-α-aminophosphonates by Sonogashira cross-coupling reaction
    Zotova, Maria A.
    Vasilyeva, Tamara P.
    Peregudov, Alexander S.
    Osipov, Sergey N.
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 135 : 33 - 37
  • [49] Visible-Light-Mediated Trifluoroethylation of N-Arylacrylamides with Trifluoroethyl Iodide: Synthesis of CF3-Containing Oxindoles
    Fu, Weijun
    Zhu, Mei
    Zou, Guanglong
    Xu, Chen
    Wang, Zhiqiang
    SYNLETT, 2014, 25 (17) : 2513 - 2517
  • [50] CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones
    Sun, Dong-Wei
    Zhou, Yong-Yan
    Jiang, Min
    Nian, Tang
    Liu, Jin-Tao
    TETRAHEDRON, 2021, 91
12345