CuI-catalyzed direct synthesis of diaryl thioethers from aryl boronic acids and arylsulfonyl chlorides

被引:14
|
作者
Huang, Keke [1 ]
Yang, Min [2 ]
Lai, Xiao-Jing [1 ]
Hu, Xin [2 ]
Qiu, Guanyinsheng [3 ]
Liu, Jin-Biao [1 ]
机构
[1] Jiangxi Univ Sci & Technol, Sch Met & Chem Engn, 86 Hongqi Rd, Ganzhou 341000, Peoples R China
[2] Gannan Med Univ, Dept Forens Sci, 1 Yixueyuan Rd, Ganzhou 341000, Jiangxi, Peoples R China
[3] Jiaxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China
关键词
aryl boronic acid; arylsulfonyl chloride; Cu(I) catalysis; thioether; C-H BOND; CROSS-COUPLINGS; SULFONYL CHLORIDES; HIGHLY EFFICIENT; S BOND; NICKEL-CATALYST; N-OXIDES; TE BOND; SULFUR; SULFENYLATION;
D O I
10.1002/aoc.5385
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A CuI-catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed. The reaction is initiated by a PPh3 reduction of the arylsulfonyl chloride, followed by a CuI-catalyzed C-S coupling with an aryl boronic acid. Various arylsulfonyl chlorides can directly serve as a sulfur source in this mild and efficient reaction giving the desired products in moderate to good yields. Moreover, this practical method has also been applied to the thioetherification of aryl iodides and acetylacetones.
引用
收藏
页数:9
相关论文
共 50 条
  • [41] Nickel-catalyzed direct formation of the C-S bonds of aryl sulfides from arylsulfonyl chlorides and aryl iodides using Mn as a reducing agent
    Wang, Yang
    Zhang, Xiaofeng
    Liu, Haixiong
    Chen, Hui
    Huang, Deguang
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01): : 31 - 36
  • [42] Direct synthesis of enaminone functionalized biaryl ethers by CuI-catalyzed O-arylation of enaminone functionalized phenols
    Wan, Jie-Ping
    Wang, Chunping
    Liu, Yunyun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6481 - 6483
  • [43] Supported Palladium-Catalyzed Carbonylative Synthesis of Diaryl Ketones from Aryl Bromides and Arylboronic Acids
    Xu, Tiefeng
    Wang, Qi
    Yang, Zeyi
    Yi, Lili
    Wang, Jian-Shu
    Lu, Wangyang
    Ying, Jun
    Wu, Xiao-Feng
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (15) : 2027 - 2030
  • [44] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    涂佩华
    JIANG Jun
    XIAO Hongping
    李新华
    Journal of Wuhan University of Technology(Materials Science), 2019, 34 (04) : 987 - 993
  • [45] Copper-catalyzed synthesis of aryl azides and 1-aryl-1,2,3-triazoles from boronic acids
    Tao, Chuan-Zhou
    Cui, Xin
    Li, Juan
    Liu, Ai-Xiang
    Liu, Lei
    Guo, Qing-Xiang
    TETRAHEDRON LETTERS, 2007, 48 (20) : 3525 - 3529
  • [46] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    Tu Peihua
    Jiang Jun
    Xiao Hongping
    Li Xinhua
    JOURNAL OF WUHAN UNIVERSITY OF TECHNOLOGY-MATERIALS SCIENCE EDITION, 2019, 34 (04): : 987 - 993
  • [47] Green Synthesis of Aryl Thioethers through Cu-catalysed C-S Coupling of Thiols and Aryl Boronic Acids in Water
    Peihua Tu
    Jun Jiang
    Hongping Xiao
    Xinhua Li
    Journal of Wuhan University of Technology-Mater. Sci. Ed., 2019, 34 : 987 - 993
  • [48] Nickel-catalyzed direct difluoromethylation of aryl boronic acids with BrCF2H
    Sheng, Jie
    Ni, Hui-Qi
    Bian, Kang-Jie
    Li, Yan
    Wang, Ning
    Wang, Xi-Sheng
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04): : 606 - 610
  • [49] Rh(I)-Catalyzed Arylation of α-Diazo Phosphonates with Aryl Boronic Acids: Synthesis of Diarylmethylphosphonates
    Zhou, Yujing
    Zhang, Yan
    Wang, Jianbo
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (05) : 621 - 627
  • [50] Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3
    Wu, Wei
    Wang, Biyun
    Ji, Xinfei
    Cao, Song
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1299 - 1303