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
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
  • [21] Tf2O-Catalyzed Tandem Cyclization/Trifluoromethylselenolation of Alkynes for Synthesis of CF3Se-Containing Heterocycles
    Zhang, Shangbiao
    Gao, Yan
    Xiao, Rui
    Li, Yang
    Wang, Yanan
    Yuan, Zheliang
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (41)
  • [22] Copper-catalyzed radical cascade cyclization for synthesis of CF3-containing tetracyclic benzimidazo[2,1-a]iso-quinolin-6(5H)-ones
    Sun, Kai
    Li, Guofeng
    Guo, Sa
    Zhang, Zhiguo
    Zhang, Guisheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (02) : 375 - 378
  • [23] Photoredox-Catalyzed Sequential Decarboxylative/Defluorinative Aminoalkylation of CF3-Alkenes with N-Arylglycines
    Xin, Hong
    Zhang, Lu
    Liao, Jinyi
    Duan, Xin-Hua
    Yang, Xu
    Guo, Li-Na
    ORGANIC LETTERS, 2024, 26 (28) : 6030 - 6034
  • [24] Photoredox-Catalyzed Tandem Radical Cyclization/Hydroxylation for the Synthesis of 4-Hydroxyalkyl-3,3-difluoro-γ-lactams
    Sun, Bin
    Zhuang, Xiaohui
    Yin, Jieli
    Zhang, Kesheng
    Zhao, Haiyun
    Jin, Can
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21) : 14177 - 14185
  • [25] Copper-Catalyzed Multicomponent Reactions of Intramolecular and Intermolecular Thiotrifluoromethylation of Alkenes: Access to CF3-Containing 2-Iminothiazolidines and Isothioureas
    Liu, Sainan
    Jiang, Liqin
    ORGANIC LETTERS, 2022, 24 (39) : 7157 - 7162
  • [26] Photoredox-Catalyzed Acylation/Cyclization of 2-Isocyanobiaryls with Oxime Esters for the Synthesis of 6-Acyl Phenanthridines
    Tang, Boxiao
    Ding, Chuan
    Ou, Min
    Liu, Yu
    Liu, Junwei
    Liu, Yilin
    CATALYSTS, 2022, 12 (11)
  • [27] Synthesis of Indole-Fused 1,4-Diazepinones via Photoredox-Catalyzed Cascade Cyclization Reaction
    Brambilla, Elisa
    Meraviglia, Silvia
    Moneta, Edoardo
    Nava, Donatella
    Rizzato, Silvia
    Abbiati, Giorgio
    Pirovano, Valentina
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (22) : 3958 - 3966
  • [28] Synthesis of CF3-Containing 2-Imidazolines and Imidazoles via a Iodide-Promoted [3+2] Cyclization Reaction
    Wang, Huamin
    Niu, Wenjing
    He, Yongjun
    Wei, Yibo
    Li, Xianxian
    Lin, Ying-Wu
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21) : 15282 - 15287
  • [29] Iron-Catalyzed Trifluoromethylation of Indole-Tethered Alkene Enables Synthesis of CF3-Containing Spiroindolenines and Tetrahydrocarbazoles
    Zhao, Yilin
    Hou, Tingting
    Zhang, Liming
    Wang, Xue
    Hou, Jingli
    Liu, Yangping
    Han, Guifang
    Song, Yuguang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (18)
  • [30] Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles
    Mou, Xue-Qing
    Wang, Min
    Ren, Liang-Chen
    Jian, Yu-Rui
    Fu, Xin-Yu
    Zheng, Hong-Yu
    Zha, Xiao
    Cui, Bao-Dong
    Zhang, Yun
    Chen, Yong-Zheng
    ORGANIC CHEMISTRY FRONTIERS, 2023, 11 (01) : 74 - 82