TfNHNHBoc as a SCF3 source for the sulfenylation of indoles

被引:23
作者
Guo, Jing-Yu
Dai, Rui-Han
Xu, Wen-Cong
Wu, Ruo-Xin
Tian, Shi-Kai [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
FREE DIRECT TRIFLUOROMETHYLTHIOLATION; ELECTRON-RICH AROMATICS; S BOND FORMATION; CATALYZED REGIOSELECTIVE THIOLATION; SULFONYL HYDRAZIDES; C-S; ARYLSULFONYL HYDRAZIDES; SODIUM TRIFLUOROMETHANESULFINATE; ASSISTED SYNTHESIS; FUNCTIONALIZATION;
D O I
10.1039/c8cc04600j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unprecedented use of trifluoromethanesulfonyl hydrazides as effective SCF3 sources has been established in the sulfenylation of indoles. A range of substituted indoles participated in CuCl-catalyzed oxidative sulfenylation reaction with TfNHNHBoc in the presence of dimethyl sulfoxide to furnish structurally diverse 3-indoyl trifluoromethyl thioethers in moderate to good yields with very high regioselectivity.
引用
收藏
页码:8980 / 8982
页数:3
相关论文
共 71 条
  • [11] SOME UNUSUAL REACTIONS OF TOLUENE-P-SULPHONHYDRAZIDE
    DEAVIN, A
    REES, CW
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1961, (NOV): : 4970 - &
  • [12] Electrophilic trifluoromethanesulfanylation of indole derivatives
    Ferry, Aurelien
    Billard, Thierry
    Bacque, Eric
    Langlois, Bernard R.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2012, 134 : 160 - 163
  • [13] First and second generation of trifluoromethanesulfenamide reagent: A trifluoromethylthiolating comparison
    Glenadel, Quentin
    Alazet, Sebastien
    Billard, Thierry
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 : 89 - 95
  • [14] TfNHNHBoc as a Trifluoromethylating Agent for Vicinal Difunctionalization of Terminal Alkenes
    Guo, Jing-Yu
    Wu, Ruo-Xin
    Jin, Ji-Kang
    Tian, Shi-Kai
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3850 - 3853
  • [15] Palladium-catalyzed thiolation of alkanes and ethers with arylsulfonyl hydrazides
    Guo, Sheng-rong
    He, Wei-ming
    Xiang, Jian-nan
    Yuan, Yan-qin
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (62) : 8578 - 8581
  • [16] C-S and C-N bond formation via Mn-promoted oxidative cascade reaction: Synthesis of C3-sulfenated indoles
    He, Lin
    Li, Xianwei
    [J]. TETRAHEDRON, 2017, 73 (43) : 6138 - 6145
  • [17] Transition-Metal-Free Trifluoromethylthiolation of N-Heteroarenes
    Honeker, Roman
    Ernst, Johannes B.
    Glorius, Frank
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (22) : 8047 - 8051
  • [18] Mechanism of action of the insecticides, lindane and fipronil, on glycine receptor chloride channels
    Islam, Robiul
    Lynch, Joseph W.
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 2012, 165 (08) : 2707 - 2720
  • [19] Direct Phosphorus-Induced Fluoroalkylthiolation with Fluoroalkylsulfonyl Chlorides
    Jiang, Lvqi
    Yi, Wenbin
    Liu, Qiran
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3700 - 3705
  • [20] Direct Trifluoromethylthiolation and Perfluoroalkylthiolation of C(sp2)-H Bonds with CF3SO2Na and RfSO2Na
    Jiang, Lvqi
    Qian, Jinlong
    Yi, Wenbin
    Lu, Guoping
    Cai, Chun
    Zhang, Wei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14965 - 14969