Borate-mediated aryl polyfluoroalkoxylation under transition-metal-free conditions

被引:3
|
作者
Kikushima, Kotaro [1 ]
Tsuda, Tomoka [1 ]
Miyamoto, Naoki [1 ]
Kita, Yasuyuki [2 ]
Dohi, Toshifumi [1 ,2 ]
机构
[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Kusatsu, Shiga 5258577, Japan
[2] Ritsumeikan Univ, Res Org Sci & Technol, Kusatsu, Shiga 5258577, Japan
关键词
SUBSTITUTION; CHLORIDES; ETHERS;
D O I
10.1039/d4cc04008b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe the transition-metal-free coupling for polyfluoroalkoxy arenes using polyfluoroalkoxy borates, which serve as counterions to diaryliodonium salts and transferring mediators of polyfluoroalkoxy groups. This strategy demonstrates high functional group compatibility owing to the low nucleophilicity of the borate mediator, thus offering a practical approach for synthesizing diverse polyfluoroalkoxy arenes. We report boron-intermediary ligand transfer of diaryliodonium salt, synthesizing polyfluorolalkyl aryl ethers in the absence of transition metal catalyst or base.
引用
收藏
页码:10552 / 10555
页数:4
相关论文
共 50 条
  • [41] Synthesis of Multiarmed Thienylene-Tetrafluorophenylene Alternating Copolymers under Transition-Metal-Free Conditions
    Sanji, Takanobu
    Kakinuma, Junko
    Iyoda, Tomokazu
    MACROMOLECULES, 2016, 49 (18) : 6761 - 6767
  • [42] NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
    Zhang, Guofu
    Fan, Qiankun
    Wang, Huimin
    Zhao, Yiyong
    Ding, Chengrong
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 833 - 837
  • [43] Transition-metal-free, visible-light-mediated cyclization of o-azidoarylalkynes with aryl diazonium salts
    Jin, Cheng
    Su, Lianzheng
    Ma, Daxi
    Cheng, Mingrong
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (23) : 14053 - 14056
  • [44] Alkoxy base-mediated transition-metal-free cross-coupling reactions of benzene with aryl halides
    Liu, Wei
    Xu, Lige
    Bi, Yanlan
    RSC ADVANCES, 2014, 4 (85): : 44943 - 44947
  • [45] Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions
    Liao, Yunfeng
    Jiang, Pengcheng
    Chen, Shanping
    Xiao, Fuhong
    Deng, Guo-Jun
    RSC ADVANCES, 2013, 3 (40): : 18605 - 18608
  • [46] Odorless, Transition-Metal-Free N-Sulfenylation of Sulfoximines with Thiosulfonates under Mild Conditions
    Kang, Xiaokang
    Wang, Helin
    Zeng, Qingle
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (47)
  • [47] Direct Amidation of Alcohols with N-Substituted Formamides under Transition-Metal-Free Conditions
    Xu, Kun
    Hu, Yanbin
    Zhang, Sheng
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (32) : 9793 - 9797
  • [48] Synthesis of pyrazoles from sulfonyl hydrazone and benzyl acrylate under transition-metal-free conditions
    Hao, Liqiang
    Wang, Zhichao
    Wang, Yangyang
    Yang, Zhaoziyuan
    Liu, Xian
    Xu, Xiaobo
    Ji, Yafei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (37) : 7611 - 7615
  • [49] Transition-Metal-Free Synthesis of Biarylmethanes from Aryl Iodides and Benzylic Ketones
    Drapeau, Martin Pichette
    Tlili, Anis
    Zaid, Yassir
    Toummini, Dounia
    Chahdi, Fouad Ouazzani
    Sotiropoulos, Jean-Marc
    Ollevier, Thierry
    Taillefer, Marc
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (66) : 17449 - 17453
  • [50] Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
    Finck, Lucie
    Oestreich, Martin
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (43) : 11061 - 11064