Photoredox-Induced Three-Component Azido- and Aminotrifluoromethylation of Alkenes

被引:178
|
作者
Dagousset, Guillaume [1 ]
Carboni, Aude [1 ]
Magnier, Emmanuel [2 ]
Masson, Geraldine [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] Univ Versailles St Quentin, Inst Lavoisier Versailles, UMR 8180, F-78035 Versailles, France
关键词
VISIBLE-LIGHT PHOTOCATALYSIS; COPPER-CATALYZED TRIFLUOROMETHYLATION; CHIRAL PHOSPHORIC-ACID; SODIUM TRIFLUOROMETHANESULFINATE; MEDIATED TRIFLUOROMETHYLATION; ASYMMETRIC-SYNTHESIS; UNACTIVATED ALKENES; BOND FORMATION; EFFICIENT; HYDROTRIFLUOROMETHYLATION;
D O I
10.1021/ol5021477
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report herein a photoredox-catalyzed azidotrifluoromethylation of alkenes. Under the optimized conditions using [Ru(bpy)(3)(PF6)(2)] as the photocatalyst and Umemoto's reagent as the CF3 source, a wide range of substituted styrenes as well as various activated and non-activated alkenes can readily be difunctionalized, affording beta-trifluoromethylated azides or amines in good yields.
引用
收藏
页码:4340 / 4343
页数:4
相关论文
共 50 条
  • [1] Photoredox-Induced Deaminative Radical-Cationic Three-Component Couplings with N-Alkylpyridinium Salts and Alkenes
    Seefeldt, Paul
    Dasi, Rajesh
    Villinger, Alexander
    Brasholz, Malte
    CHEMPHOTOCHEM, 2021, 5 (11) : 979 - 983
  • [2] Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    ORGANIC LETTERS, 2014, 16 (04) : 1240 - 1243
  • [3] Direct intermolecular three-component aminotrifluoromethylation of styrenes by visible-light-photoredox catalysis
    Zheng, Lvyin
    Cai, Liuhuan
    Zhuo, Xiaoya
    Deng, Lei
    Wu, Yingying
    Yang, Beining
    Wang, Yihan
    Guo, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6498 - 6504
  • [4] Photoredox-Catalyzed Three-Component Amidoheteroarylation of Unactivated Alkenes
    Zhang, Mengxuan
    Zhang, Ji
    Zhou, Yuchen
    He, Yuxuan
    Wu, Jie
    Zheng, Danqing
    ORGANIC LETTERS, 2023, 25 (22) : 4113 - 4118
  • [5] Dual Photoredox/Nickel-Catalyzed Three-Component Carbofunctionalization of Alkenes
    Garcia-Dominguez, Andres
    Mondal, Rahul
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) : 12286 - 12290
  • [6] Three-component difluoroalkylamination of alkenes mediated by photoredox and iron cooperative catalysis
    Xu, Rui
    Cai, Chun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (37) : 8541 - 8545
  • [7] Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines
    Chen, Jian-Qiang
    Yu, Wan-Lei
    Wei, Yun-Long
    Li, Teng-Hui
    Xu, Peng-Fei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 243 - 249
  • [8] Dual Photoredox/Copper Catalysis Enabled Three-Component Defluorinative Alkylboration of Alkenes
    Ye, Tian
    Wang, Yifeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 663 - 664
  • [9] Photoredox/Copper Dual-Catalyzed Three-Component Perfluoroalkyl Trifluoromethylthiolation of Alkenes
    Guo, Kang
    Liu, Shaomian
    Yang, Yutong
    Xu, Fang
    Lu, Yongchao
    Shang, Jiayi
    Song, Aizhen
    ORGANIC LETTERS, 2025, 27 (08) : 1994 - 1998
  • [10] Three-Component Photoredox-Mediated Chloro-, Bromo-, or Iodotrifluoromethylation of Alkenes
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    SYNTHESIS-STUTTGART, 2015, 47 (16): : 2439 - 2445