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

被引:253
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
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 44 条
  • [31] Sato K., 2009, ORG SYNTH, V11, P336
  • [32] Trifluoromethylation of Organic Compounds and Related Reactions
    Sato, Kazuyuki
    Tarui, Atsushi
    Omote, Masaaki
    Ando, Akira
    Kumadaki, Itsumaro
    [J]. SYNTHESIS-STUTTGART, 2010, (11): : 1865 - 1882
  • [33] Mechanistic Studies on α-Trifluoromethylation of Ketones via Silyl Enol Ethers and Its Application to Other Carbonyl Compounds
    Sato, Kazuyuki
    Yuki, Takashi
    Yamaguchi, Ryoji
    Hamano, Tetsuya
    Tarui, Atsushi
    Omote, Masaaki
    Kumadaki, Itsumaro
    Ando, Akira
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3815 - 3819
  • [34] Selective C-H Borylation of Alkenes by Palladium Pincer Complex Catalyzed Oxidative Functionalization
    Selander, Nicklas
    Willy, Benjamin
    Szabo, Kalman J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (24) : 4051 - 4053
  • [35] Simple, Stable, and Easily Accessible Well-Defined CuCF3 Aromatic Trifluoromethylating Agents
    Tomashenko, Olesya A.
    Escudero-Adan, Eduardo C.
    Martinez Belmonte, Marta
    Grushin, Vladimir V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7655 - 7659
  • [36] ATOM ECONOMY - A CHALLENGE FOR ORGANIC-SYNTHESIS - HOMOGENEOUS CATALYSIS LEADS THE WAY
    TROST, BM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (03) : 259 - 281
  • [37] ARENESELENOLATE-MEDIATED PERFLUOROALKYL-SULFENYLATION OF ENOL ETHERS
    UNEYAMA, K
    KITAGAWA, K
    [J]. TETRAHEDRON LETTERS, 1991, 32 (28) : 3385 - 3386
  • [38] 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
  • [39] 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 - +
  • [40] Formation of ArF from LPdAr(F): Catalytic Conversion of Aryl Triflates to Aryl Fluorides
    Watson, Donald A.
    Su, Mingjuan
    Teverovskiy, Georgiy
    Zhang, Yong
    Garcia-Fortanet, Jorge
    Kinzel, Tom
    Buchwald, Stephen L.
    [J]. SCIENCE, 2009, 325 (5948) : 1661 - 1664