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 75 条
  • [31] Direct Trifluoromethylation of the CH Bond
    Liu, Hui
    Gu, Zhenhua
    Jiang, Xuefeng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) : 617 - 626
  • [32] Copper-Catalyzed Trifluoromethylation-Initiated Radical 1,2-Aryl Migration in ,-Diaryl Allylic Alcohols
    Liu, Xiaowu
    Xiong, Fei
    Huang, Xuanping
    Xu, Liang
    Li, Pengfei
    Wu, Xiaoxing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (27) : 6962 - 6966
  • [33] The New Age of Electrophilic Perfluoroalkylation Reactions
    Mace, Yohan
    Magnier, Emmanuel
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (13) : 2479 - 2494
  • [34] Mechanistical insight into 'electrophilic' trifluoromethylation with S-(trifluoromethyl)dibenzothiophenium salts
    Mace, Yohan
    Pradet, Charlotte
    Popkin, Matthew
    Blazejewski, Jean-Claude
    Magnier, Emmanuel
    [J]. TETRAHEDRON LETTERS, 2010, 51 (41) : 5388 - 5391
  • [35] A Photo Touch on Amines: New Synthetic Adventures of Nitrogen Radical Cations
    Maity, Soumitra
    Zheng, Nan
    [J]. SYNLETT, 2012, (13) : 1851 - 1856
  • [36] One-Pot Synthesis of Hypervalent Iodine Reagents for Electrophilic Trifluoromethylation
    Matousek, Vaclav
    Pietrasiak, Ewa
    Schwenk, Rino
    Togni, Antonio
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13) : 6763 - 6768
  • [37] Addition of CF3 across unsaturated moieties: a powerful functionalization tool
    Merino, Estibaliz
    Nevado, Cristina
    [J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (18) : 6598 - 6608
  • [38] Mita T., 2005, [No title captured], Patent No. [JP2005272452, 2005272452]
  • [39] Mita T., 2004, Patent WO 2004018410 A1, Patent No. 2004018410
  • [40] Catalytic Hydrotrifluoromethylation of Unactivated Alkenes
    Mizuta, Satoshi
    Verhoog, Stefan
    Engle, Keary M.
    Khotavivattana, Tanatorn
    O'Duill, Miriam
    Wheelhouse, Katherine
    Rassias, Gerasimos
    Medebielle, Maurice
    Gouverneur, Veronique
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (07) : 2505 - 2508