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
  • [21] Iodine-Mediated Thiolation of Substituted Naphthols/Naphthylamines and Arylsulfonyl Hydrazides via C(sp2)-H Bond Functionalization
    Kang, Xing
    Yan, Rulong
    Yu, Guiqin
    Pang, Xiaobo
    Liu, Xingxing
    Li, Xiaoni
    Xiang, Likui
    Huang, Guosheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10605 - 10610
  • [22] Copper-Catalyzed Aerobic Oxidative N-S Bond Functionalization for C-S Bond Formation: Regio-and Stereoselective Synthesis of Sulfones and Thioethers
    Li, Xianwei
    Xu, Yanli
    Wu, Wanqing
    Jiang, Chang
    Qi, Chaorong
    Jiang, Huanfeng
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (26) : 7911 - 7915
  • [23] Catalytic asymmetric sulfenylation to structurally diverse dithioketals
    Liao, Kui
    Zhou, Feng
    Yu, Jin-Sheng
    Gao, Wei-Ming
    Zhou, Jian
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (90) : 16255 - 16258
  • [24] Transition metal-free direct trifluoromethylthiolation of indoles using trifluoromethanesulfonyl chloride in the presence of triphenylphosphine
    Lu, Kui
    Deng, Zhijie
    Li, Ming
    Li, Tianjiao
    Zhao, Xia
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (05) : 1254 - 1260
  • [25] BrOsted acid-catalyzed electrophilic trifluoromethylthiolation of indoles using thermally stable trifluoromethylthiolating reagent
    Ma, Bingqing
    Shao, Xinxin
    Shen, Qilong
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2015, 171 : 73 - 77
  • [26] Direct electrophilic trifluoromethylthiolation of N-benzyl indoles using AgSCF3
    Ma, Lan
    Cheng, Xiu-Fen
    Li, Yan
    Wang, Xi-Sheng
    [J]. TETRAHEDRON LETTERS, 2016, 57 (27-28) : 2972 - 2975
  • [27] Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines
    Meesin, Jatuporn
    Pohmakotr, Manat
    Reutrakul, Vichai
    Soorukram, Darunee
    Leowanawat, Pawaret
    Kuhakarn, Chutima
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3662 - 3669
  • [28] CeCl3•7H2O-NaI Promoted Regioselective Sulfenylation of Indoles with Sulfonylhydrazides
    Nookaraju, U.
    Begari, Eeshwaraiah
    Yetra, Ravikiran Reddy
    Kumar, Pradeep
    [J]. CHEMISTRYSELECT, 2016, 1 (01): : 81 - 85
  • [29] Iodine-Mediated Synthesis of Aromatic Thioethers with Aromatic Amines and Sulfonyl Hydrazides in High Regioselectivity via C(sp2)-H Bond Functionalization
    Pang, Xiaobo
    Xiang, Likui
    Yang, Xiaodong
    Yan, Rulong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 321 - 325
  • [30] Copper(I) Bromide-Dimethyl Sulfide-Catalyzed Direct Sulfanylation of 4-Hydroxycoumarins and 4-Hydroxyquinolinones with Arylsulfonylhydrazides and Selective Fluorescence Switch-On Sensing of Cadmium(II) Ion in Water
    Paul, Sanjay
    Shrestha, Rajeev
    Edison, T. N. J. I.
    Lee, Yong Rok
    Kim, Sung Hong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (19) : 3050 - 3056