Palladium-Catalyzed Oxidative Aryltrifluoromethylation of Activated Alkenes at Room Temperature

被引:455
作者
Mu, Xin [1 ]
Wu, Tao [1 ]
Wang, Hao-yang [2 ]
Guo, Yin-long [2 ]
Liu, Guosheng [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Mass Spectrometry Ctr, Shanghai 200032, Peoples R China
关键词
FORMING REDUCTIVE ELIMINATION; BOND-FORMATION; ARYL IODIDES; C-O; TRIFLUOROMETHYLATION; DIAMINATION; FLUORINE; CONSTRUCTION; OXINDOLES; PD;
D O I
10.1021/ja210614y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed intramolecular oxidative aryltrifluoromethylation reaction of activated alkenes has been explored. The reaction allows for an efficient synthesis of a variety of CF3-containing oxindoles. Preliminary mechanistic study indicated that the reaction involves a C-sp(3)-Pd-IV(CF3) intermediate, which undergoes reductive elimination to afford a C-sp(3)-CF3 bond.
引用
收藏
页码:878 / 881
页数:4
相关论文
共 73 条
  • [61] Copper-Catalyzed C(sp3)-C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation
    Wang, Xi
    Ye, Yuxuan
    Zhang, Songnan
    Feng, Jiajie
    Xu, Yan
    Zhang, Yan
    Wang, Jianbo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) : 16410 - 16413
  • [62] Pd(II)-Catalyzed ortho-Trifluoromethylation of Arenes Using TFA as a Promoter
    Wang, Xisheng
    Truesdale, Larry
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3648 - +
  • [63] Iodo-Carbocyclization of Electron-Deficient Alkenes: Synthesis of Oxindoles and Spirooxindoles
    Wei, Hai-Long
    Piou, Tiffany
    Dufour, Jeremy
    Neuville, Luc
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2011, 13 (09) : 2244 - 2247
  • [64] Welch J.T., 1991, FLUORINE BIOORGANIC
  • [65] Cooperative Effect of Silver in Copper-Catalyzed Trifluoromethylation of Aryl Iodides Using Me3SiCF3
    Weng, Zhiqiang
    Lee, Richmond
    Jia, Weiguo
    Yuan, Yaofeng
    Wang, Wenfeng
    Feng, Xue
    Huang, Kuo-Wei
    [J]. ORGANOMETALLICS, 2011, 30 (11) : 3229 - 3232
  • [66] Palladium-Catalyzed Intramolecular Aminofluorination of Unactivated Alkenes
    Wu, Tao
    Yin, Guoyin
    Liu, Guosheng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) : 16354 - +
  • [67] Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C-H Bond Activation
    Xu, Jun
    Fu, Yao
    Luo, Dong-Fen
    Jiang, Yuan-Ye
    Xiao, Bin
    Liu, Zhao-Jing
    Gong, Tian-Jun
    Liu, Lei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) : 15300 - 15303
  • [68] Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent
    Xu, Jun
    Luo, Dong-Fen
    Xiao, Bin
    Liu, Zhao-Jing
    Gong, Tian-Jun
    Fu, Yao
    Liu, Lei
    [J]. CHEMICAL COMMUNICATIONS, 2011, 47 (14) : 4300 - 4302
  • [69] Oxidation of a Cyclometalated Pd(II) Dimer with "CF3+": Formation and Reactivity of a Catalytically Competent Monomeric Pd(IV) Aquo Complex
    Ye, Yingda
    Ball, Nicholas D.
    Kampf, Jeff W.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14682 - 14687
  • [70] Copper-Mediated Trifluoromethylation of Heteroaromatic Compounds by Trifluoromethyl Sulfonium Salts
    Zhang, Cheng-Pan
    Wang, Zong-Ling
    Chen, Qing-Yun
    Zhang, Chun-Tao
    Gu, Yu-Cheng
    Xiao, Ji-Chang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (08) : 1896 - 1900