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
  • [1] Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
    Alix, Aurelien
    Lalli, Claudia
    Retailleau, Pascal
    Masson, Geraldine
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10389 - 10392
  • [2] [Anonymous], 2008, BIOORGAN MED CHEM
  • [3] Metal-Free Dioxygenation of Enecarbamates Mediated by a Hypervalent Iodine Reagent
    Bekkaye, Mathieu
    Su, Yingpeng
    Masson, Geraldine
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) : 3978 - 3982
  • [4] Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates
    Carboni, Aude
    Dagousset, Guillaume
    Magnier, Emmanuel
    Masson, Geraldine
    [J]. ORGANIC LETTERS, 2014, 16 (04) : 1240 - 1243
  • [5] Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations
    Chen, Pinhong
    Liu, Guosheng
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (21): : 2919 - 2939
  • [6] Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols
    Chen, Zhi-Min
    Bai, Wei
    Wang, Shao-Hua
    Yang, Bin-Miao
    Tu, Yong-Qiang
    Zhang, Fu-Min
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9781 - 9785
  • [7] Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction
    Courant, Thibaut
    Masson, Geraldine
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) : 423 - 427
  • [8] Chiral Phosphoric Acid-Catalyzed Enantioselective Three-Component Povarov Reaction Using Enecarbamates as Dienophiles: Highly Diastereo- and Enantioselective Synthesis of Substituted 4-Aminotetrahydroquinolines
    Dagousset, Guillaume
    Zhu, Jieping
    Masson, Geraldine
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (37) : 14804 - 14813
  • [9] Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones
    Deb, Arghya
    Manna, Srimanta
    Modak, Atanu
    Patra, Tuhin
    Maity, Soham
    Maiti, Debabrata
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9747 - 9750
  • [10] Iron Chloride-Catalyzed Three-Component Domino Sequences: Syntheses of Functionalized α-Oxy-N-acylhemiaminals and α-Oxyimides
    Drouet, Fleur
    Zhu, Jieping
    Masson, Geraldine
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3563 - 3569
12345678