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
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 16期
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 75 条
  • [61] Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3
    Wu, Xinyue
    Chu, Lingling
    Qing, Feng-Ling
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) : 2198 - 2202
  • [62] Synthetic applications of photoredox catalysis with visible light
    Xi, Yumeng
    Yi, Hong
    Lei, Aiwen
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (15) : 2387 - 2403
  • [63] Recent advance in transition-metal-mediated trifluoromethylation for the construction of C(sp3)-CF3 bonds
    Xu, Jun
    Liu, Xiaoyang
    Fu, Yao
    [J]. TETRAHEDRON LETTERS, 2014, 55 (03) : 585 - 594
  • [64] Visible-Light-Induced Trifluoromethylation of N-Aryl Acrylamides: A Convenient and Effective Method To Synthesize CF3-Containing Oxindoles Bearing a Quaternary Carbon Center
    Xu, Pan
    Xie, Jin
    Xue, Qicai
    Pan, Changduo
    Cheng, Yixiang
    Zhu, Chengjian
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) : 14039 - 14042
  • [65] Iron- Catalyzed 1,2-Addition of Perfluoroalkyl Iodides to Alkynes and Alkenes
    Xu, Tao
    Cheung, Chi Wai
    Hu, Xile
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) : 4910 - 4914
  • [66] Visible-Light Photoredox Catalysis
    Xuan, Jun
    Xiao, Wen-Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) : 6828 - 6838
  • [67] Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    [J]. ORGANIC LETTERS, 2013, 15 (09) : 2136 - 2139
  • [68] Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9567 - 9571
  • [69] Visible Light Photocatalysis: The Development of Photocatalytic Radical Ion Cycloadditions
    Yoon, Tehshik P.
    [J]. ACS CATALYSIS, 2013, 3 (05): : 895 - 902
  • [70] Yoon TP, 2010, NAT CHEM, V2, P527, DOI [10.1038/NCHEM.687, 10.1038/nchem.687]
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