Electrophilic Trifluoromethylation by Copper-Catalyzed Addition of CF3-Transfer Reagents to Alkenes and Alkynes

被引：250
|
作者：
Janson, Par G. [1 ]
Ghoneim, Ibrahim [1 ]
Ilchenko, Nadia O. [1 ]
Szabo, Kalman J. [1 ]
机构：
[1] Stockholm Univ, Dept Organ Chem, SE-10691 Stockholm, Sweden
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 11期
基金：
瑞典研究理事会;
关键词：
ALPHA-TRIFLUOROMETHYLATION; TERMINAL ALKENES; CHEMISTRY; FLUORINE; POSITION; ETHERS; ARENES;
D O I：
10.1021/ol3011419
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regio- and stereoselective Cu-catalyzed addition of the above hypervalent iodine reagent to alkynes and alkenes was achieved. In the presence of Cul, the reaction is suitable to perform trifluoromethyl-benzoyloxylation and trifluoromethyl-halogenation of alkenes and alkynes. Electron-donating substituents accelerate the process, and alkenes react faster than alkynes emphasizing the electrophilic character of the addition reaction.
引用
收藏
页码：2882 / 2885
页数：4
相关论文
共 50 条
  • [1] Trifluoromethylation by copper-catalyzed reaction of CF3-transfer reagents with alkenes and alkynes
    Szabo, Kalman J.
    Janson, Par
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [2] Copper-catalyzed trifluoromethylation of alkenes and alkynes
    Janson, Par G.
    Ilchenko, Nadia O.
    Ghoneim, Ibrahim
    Szabo, Kalman J.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [3] Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent
    Wang, Xiao-Ping
    Lin, Jin-Hong
    Zhang, Cheng-Pan
    Xiao, Ji-Chang
    Zheng, Xing
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2635 - 2640
  • [4] Copper-Catalyzed Regioselective Oxytrifluoromethylation of Allenes Using a CF3-Transfer Reagent
    Wang, Yanan
    Jiang, Min
    Liu, Jin-Tao
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2907 - 2912
  • [5] Copper-catalyzed trifluoromethylation of organic zinc reagents with an electrophilic trifluoromethylating reagent
    Wang, Chang-Sheng
    Wang, Haoyang
    Yao, Cheng
    [J]. RSC ADVANCES, 2015, 5 (31) : 24783 - 24787
  • [6] Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents
    Hirano, Koji
    Miura, Masahiro
    [J]. PURE AND APPLIED CHEMISTRY, 2014, 86 (03) : 291 - 297
  • [7] Mild copper-catalyzed trifluoromethylation of terminal alkynes using an electrophilic trifluoromethylating reagent
    Weng, Zhiqiang
    Li, Huaifeng
    He, Weiming
    Yao, Liang-Feng
    Tan, Jianwei
    Chen, Jinfa
    Yuan, Yaofeng
    Huang, Kuo-Wei
    [J]. TETRAHEDRON, 2012, 68 (11) : 2527 - 2531
  • [8] Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes
    [J]. Gaunt, M.J. (mjg32@cam.ac.uk), 1600, American Chemical Society (135):
  • [9] Copper-Catalyzed Electrophilic Carbofunctionalization of Alkynes to Highly Functionalized Tetrasubstituted Alkenes
    Suero, Marcos G.
    Bayle, Elliott D.
    Collins, Beatrice S. L.
    Gaunt, Matthew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) : 5332 - 5335
  • [10] Activation of diboron reagents: Catalytic copper-catalyzed borylation of electrophilic alkenes
    Santos, Webster L.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
12345