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
  • [1] Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates
    Mao, Yihui
    Wang, Xiangquan
    Zhong, Chengcheng
    Jin, Jinkang
    Lu, Zhan
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (16): : 4464 - 4469
  • [2] Anti-Diastereoselective Synthesis of CF3-Containing Spirooxazolines and Spirooxazines via Regiospecific Trifluoromethylative Spirocyclization by Photoredox Catalysis
    Noto, Naoki
    Miyazawa, Kazuki
    Koike, Takashi
    Akita, Munetaka
    ORGANIC LETTERS, 2015, 17 (15) : 3710 - 3713
  • [3] Photoredox-catalyzed halotrifluoromethylations of alkynes with triethylammonium halides: synthesis of tetrasubstituted alkenes containing CF3and halogens
    Lee, Woori
    Lee, Yeonhee
    Yoo, Minjin
    Han, Soo Bong
    Kim, Hyun Jin
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (20): : 3209 - 3214
  • [4] Visible-Light Photoredox-Catalyzed Tandem Trifluoro-methylation/Cyclization/Remote Oxidation of 1,6-Dienes: Access to CF3-Containing Five-Membered Heterocycles
    Chun, Jianlin
    Zhang, Honglin
    Meng, Fei
    Guo, Kang
    Cao, Shujun
    Fang, Qin
    Li, Jie
    Zhu, Yingguang
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 751 - 756
  • [5] Synthesis of SCF3-Containing Benzoxazines and Oxazolines via a Photoredox-Catalyzed Radical Trifluoromethylthiolation-Cyclization of Olefinic Amides
    Zhu, Mei
    Li, Rongxia
    You, Qingqing
    Fu, Weijun
    Guo, Weisi
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (11) : 2002 - 2005
  • [6] Synthesis of ester-containing phenanthridines via photoredox-catalyzed radical cascade cyclization of N-arylacrylamides with alkyloxalyl chlorides
    Chen, Meiling
    Chen, Jian-Qiang
    Chen, Zhengkai
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (16) : 3995 - 4001
  • [7] Electrochemical oxidative cyclization of N-allylamides for the synthesis of CF3-containing benzoxazines and oxazolines
    Li, Yutian
    Wang, Li
    Zhou, Shengbin
    He, Guoxue
    Zhou, Yu
    RSC ADVANCES, 2024, 14 (01) : 154 - 159
  • [8] Regioselective Synthesis of Indole-Fused Seven-Membered N-Heterocycles via Photoredox-Catalyzed Intramolecular Cyclization
    Zhang, Ziqin
    Chen, Yifeng
    He, Linrong
    Xie, Lihua
    Chen, Zhitao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21) : 14394 - 14406
  • [9] Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade
    Shu, Chao
    Noble, Adam
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) : 3870 - 3874
  • [10] Synthesis of Phenanthrenes through Visible-Light Photoredox Catalyzed Intramolecular Cyclization of -Bromochalcones
    Nagode, Savita B.
    Kant, Ruchir
    Rastogi, Namrata
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (13) : 1533 - 1537
12345