Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

被引:45
|
作者
Cloutier, Melissa [1 ]
Roudias, Majdouline [1 ]
Paquin, Jean-Francois [1 ]
机构
[1] Univ Laval, Dept Chim, PROTEO, CGCC, 1045 Ave Med, Quebec City G1V 0A6, PQ, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
ALPHA-TRIFLUOROMETHYLATED KETONES; FACILE SYNTHESIS; HYDROALKOXYLATION; ACID; CHEMISTRY; FLUORINE; ALKYNES; ACCESS;
D O I
10.1021/acs.orglett.9b01379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
引用
收藏
页码:3866 / 3870
页数:5
相关论文
共 50 条
  • [1] Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes
    Sun, Sheng
    Kroll, Julien
    Luo, Yingdong
    Zhang, Liming
    SYNLETT, 2012, 23 (01) : 54 - 56
  • [2] Direct Gold-Catalyzed Regioselective Tetrafunctionalization of Nonactivated Alkynes
    Wei, Fang
    Wang, Xianghua
    Peng, Shasha
    Jia, Qiuhui
    Jiang, Chao
    Liu, Shili
    Xu, Zhenghu
    SYNTHESIS-STUTTGART, 2014, 46 (16): : 2168 - 2174
  • [3] Stereo- and Regioselective Gold-Catalyzed Hydroamination of Internal Alkynes with Dialkylamines
    Hesp, Kevin D.
    Stradiotto, Mark
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) : 18026 - 18029
  • [4] Gold-catalyzed hydroarylation of alkynes
    Reetz, MT
    Sommer, K
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (18) : 3485 - 3496
  • [5] Regioselective synthesis of oxepinones and azepinones by gold-catalyzed cycloisomerization of functionalyzed cyclopropyl alkynes
    Fernandez-Garcia, Jesus M.
    Garcia-Garcia, Patricia
    Fernandez-Rodriguez, Manuel A.
    Perez-Anes, Alexandra
    Aguilar, Enrique
    CHEMICAL COMMUNICATIONS, 2013, 49 (95) : 11185 - 11187
  • [6] Highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides
    Hamel, Jean-Denys
    Hayashi, Tatsuru
    Cloutier, Melissa
    Savoie, Paul R.
    Thibeault, Olivier
    Beaudoin, Meggan
    Paquin, Jean-Francois
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (46) : 9830 - 9836
  • [7] Exploiting the inductive effect of the trifluoromethyl group: regioselective gold-catalyzed hydration of 2,2,2-trifluoroethyl-substituted alkynes
    Gauthier, Raphael
    Tzouras, Nikolaos V.
    Nolan, Steven P.
    Paquin, Jean-Francois
    CHEMICAL COMMUNICATIONS, 2023, 59 (59) : 9138 - 9141
  • [8] Gold-Catalyzed Hydrohydrazidation of Terminal Alkynes
    Zimin, Dmitry P.
    Dar'in, Dmitry V.
    Rassadin, Valentin A.
    Kukushkin, Vadim Yu.
    ORGANIC LETTERS, 2018, 20 (16) : 4880 - 4884
  • [9] Gold-Catalyzed Carbazolation Reactions of Alkynes
    Jana, Sripati
    He, Feifei
    Koenigs, Rene M.
    ORGANIC LETTERS, 2020, 22 (12) : 4873 - 4877
  • [10] Ambiphilic Reactivity of SF5-Alkynes Applied to Regioselective and Stereodivergent Halogenation Reactions: An Experimental and Theoretical Case Study
    Matchavariani, David
    Popek, Lucas
    Cabrera-Trujillo, Jorge Juan
    Nguyen, Thi Mo
    Blanchard, Nicolas
    Miqueu, Karinne
    Cahard, Dominique
    Bizet, Vincent
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (16) : 3481 - 3493