Trifluoromethylsulfonyl pyridinium salt for trifluoromethythiolation of indoles

被引:1
作者
Yang, Xin-Jun [1 ]
Lin, Jin-Hong [1 ,2 ]
Xiao, Ji-Chang [1 ]
机构
[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Chinese Acad Sci, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China
基金
中国国家自然科学基金;
关键词
Trifluoromethylsulfonyl pyridinium salt; Trifluoromethylthiolation; Indoles; Fluorine; Trifluoromethanesulfonic anhydride; FREE DIRECT TRIFLUOROMETHYLTHIOLATION; HYPERVALENT IODINE REAGENT; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; SODIUM TRIFLUOROMETHANESULFINATE; DIFLUOROCARBENE; CF3SO2NA; INSIGHT;
D O I
10.1016/j.jfluchem.2022.110047
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The trifluoromethylsulfonyl pyridinium salt (TFSP) was used as a CF3S source for the trifluoromethylthiolation of indole derivatives. It is proposed that TFSP is reduced in the presence of diethyl phosphite and NaCl. The pro-tocol features a facile access to the CF3S source, and high efficiency and transition-metal free conditions for trifluoromethylthiolation.
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页数:8
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共 40 条
  • [1] Electrophilic Trifluoromethylthiolation of Carbonyl Compounds
    Alazet, Sebastien
    Zimmer, Luc
    Billard, Thierry
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) : 8589 - 8593
  • [2] N-Trifluoromethylthiophthalimide: A Stable Electrophilic SCF3-Reagent and its Application in the Catalytic Asymmetric Trifluoromethylsulfenylation
    Bootwicha, Teerawut
    Liu, Xiangqian
    Pluta, Roman
    Atodiresei, Iuliana
    Rueping, Magnus
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (49) : 12856 - 12859
  • [3] Transition-metal-free electrophilic trifluoromethylthiolation with sodium trifluoromethanesulfinate at room temperature
    Bu, Mei-jie
    Lu, Guo-ping
    Cai, Chun
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 266 - 270
  • [4] Interrupted reduction of CF3SO2CL using tricyclohexylphosphine allows for electrophilic trifluoromethylsulfinylation
    Chachignon, Helene
    Cahard, Dominique
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2017, 198 : 82 - 88
  • [5] Novel Use of CF3SO2Cl for the Metal-Free Electrophilic Trifluoromethylthiolation
    Chachignon, Helene
    Maeno, Mayaka
    Kondo, Hiroya
    Shibata, Norio
    Cahard, Dominique
    [J]. ORGANIC LETTERS, 2016, 18 (10) : 2467 - 2470
  • [6] CEFAZAFLUR, A NEW PARENTERAL CEPHALOSPORIN - INVITRO STUDIES
    COUNTS, GW
    GREGORY, D
    ZELEZNIK, D
    TURCK, M
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1977, 11 (04) : 708 - 711
  • [7] Electrophilic trifluoromethanesulfanylation of indole derivatives
    Ferry, Aurelien
    Billard, Thierry
    Bacque, Eric
    Langlois, Bernard R.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2012, 134 : 160 - 163
  • [8] Synthesis of Trifluoromethanesulfinamidines and -sulfanylamides
    Ferry, Aurelien
    Billard, Thierry
    Langlois, Bernard R.
    Bacque, Eric
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (23) : 9362 - 9365
  • [9] Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by PIII/PV=O Redox Cycling
    Ghosh, Avipsa
    Lecomte, Morgan
    Kim-Lee, Shin-Ho
    Radosevich, Alexander T.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (09) : 2864 - 2869
  • [10] TfNHNHBoc as a SCF3 source for the sulfenylation of indoles
    Guo, Jing-Yu
    Dai, Rui-Han
    Xu, Wen-Cong
    Wu, Ruo-Xin
    Tian, Shi-Kai
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (65) : 8980 - 8982