Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides

被引:26
|
作者
Luo, Ziwei [1 ]
Yang, Xinkan [1 ]
Tsui, Gavin Chit [1 ]
机构
[1] Chinese Univ Hong Kong, Dept Chem, Shatin, Hong Kong, Peoples R China
关键词
METAL-FREE TRIFLUOROMETHYLTHIOLATION; ARYL BORONIC ACIDS; DECARBOXYLATIVE TRIFLUOROMETHYLTHIOLATION; CATALYZED TRIFLUOROMETHYLTHIOLATION; SILVER(I) TRIFLUOROMETHANETHIOLATE; NUCLEOPHILIC TRIFLUOROMETHYLATION; SUBSTITUENT CONSTANTS; TERMINAL ALKYNES; FLUORINE; TRIMETHYLSILANE;
D O I
10.1021/acs.orglett.0c02235
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical synthesis of perfluoroalkyl sulfides is described. The method employs stable and readily accessible thiosulfonates as new electrophiles with commercial nucleophilic perfluoroalkylating reagents. The mild reaction conditions allow access to a wide variety of both aryl- and alkyl-substituted perfluoroalkyl sulfides amenable to pharmaceutical development. Furthermore, the reaction operation is straightforward, odorless, does not produce toxic wastes, and, therefore should appeal to practitioners in industrial-scale productions.
引用
收藏
页码:6155 / 6159
页数:5
相关论文
共 50 条
  • [1] Perfluoroalkylation of 2-mercaptoethanol as a key step for a new synthesis of perfluoroalkyl vinyl sulfides, sulfoxides and sulfones
    Magnier, E
    Tordeux, M
    Goumont, W
    Magder, K
    Wakselman, C
    JOURNAL OF FLUORINE CHEMISTRY, 2003, 124 (01) : 55 - 59
  • [2] Synthesis of quaternary α-perfluoroalkyl lactams via electrophilic perfluoroalkylation
    Katayev, D.
    Vaclavik, J.
    Bruening, F.
    Commare, B.
    Togni, A.
    CHEMICAL COMMUNICATIONS, 2016, 52 (21) : 4049 - 4052
  • [3] Sequential perfluoroalkylation and asymmetric reduction of nitriles triggered with perfluoroalkyl titanates: catalytic asymmetric synthesis of perfluoroalkyl amines
    Mikami, Koichi
    Murase, Tatsushi
    Zhai, Lili
    Kawauchi, Susumu
    Itoh, Yoshimitsu
    Ito, Shigekazu
    TETRAHEDRON LETTERS, 2010, 51 (10) : 1371 - 1373
  • [4] Transition-Metal-Free Perfluoroalkylation of N-Thiophthalimides and N-Thioimides to Access Perfluoroalkyl Sulfides
    Liu, Wenting
    Qian, Han
    Song, Zijie
    Liu, Yong
    Peng, Jiajian
    Sun, Wen-Wu
    Shao, Xinxin
    Bai, Ying
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (36)
  • [5] Synthesis of Perfluoroalkyl-Substituted Oxindoles through Organophotoredox-Catalyzed Perfluoroalkylation of N -arylacrylamides with Perfluoroalkyl Iodides
    Yang, Zhiyong
    Tang, Anjiang
    SYNLETT, 2019, 30 (09) : 1061 - 1066
  • [6] Synthesis of cyclic sulfides by nickel complexes catalyzed electroreduction of unsaturated thioacetates and thiosulfonates
    Ozaki, S
    Matsui, E
    Saiki, T
    Yoshinaga, H
    Ohmori, H
    TETRAHEDRON LETTERS, 1998, 39 (44) : 8121 - 8124
  • [7] Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides
    Sipyagin, AM
    Enshov, VS
    Kashtanov, SA
    Potemkin, VA
    Trasher, JS
    Waterfeld, A
    RUSSIAN CHEMICAL BULLETIN, 2004, 53 (02) : 420 - 434
  • [8] Synthesis of aryl perfluoroalkyl sulfides from aromatic disulfides
    A. M. Sipyagin
    V. S. Enshov
    S. A. Kashtanov
    V. A. Potemkin
    J. S. Thrasher
    A. Waterfeld
    Russian Chemical Bulletin, 2004, 53 : 420 - 434
  • [9] Synthesis of perfluoroalkyl thioethers from aromatic thiocyanates by iron-catalysed decarboxylative perfluoroalkylation
    Exner, Benjamin
    Bayarmagnai, Bilguun
    Matheis, Christian
    Goossen, Lukas J.
    JOURNAL OF FLUORINE CHEMISTRY, 2017, 198 : 89 - 93
  • [10] Perfluoroalkylation of Unactivated Alkenes with Acid Anhydrides as the Perfluoroalkyl Source
    Kawamura, Shintaro
    Sodeoka, Mikiko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8740 - 8743