Synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)3

被引：1
作者：
Ma, Cui-Cui [1 ]
Zhu, Xing-Xing [1 ]
Liu, Li [1 ]
Dai, Jian-Jun [1 ]
Xu, Jun [1 ]
Xu, Hua-Jian [1 ]
机构：
[1] Hefei Univ Technol, Sch Food & Biol Engn, Hefei 230009, Peoples R China
来源：
TETRAHEDRON LETTERS | 2021年 / 82卷
基金：
中国国家自然科学基金;
关键词：
C-F bond; Polyfluorinated aromatic ethers; Polyfluorinated aromatic thioethers; B(C6F5)(3); SNAr; FRUSTRATED LEWIS PAIRS; ARYL HALIDES; O-ARYLATION; PHENOLS; HYDROSILATION; HYDROGENATION; TRIS(PENTAFLUOROPHENYL)BORANE; 1,1-CARBOBORATION; POLYFLUOROARENES; ALKOXYLATION;
D O I：
10.1016/j.tetlet.2021.153387
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise and efficient method for the synthesis of polyfluorinated aromatic ethers and thioethers by synergistic cleavage of C-B bond and C-F bond of B(C6F5)(3) is reported. The reaction could proceed smoothly with excellent functional-group compatibility. In addition, the transformation represents the first general application of B(C6F5)(3) as reaction partners in cross-coupling reaction. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：6
相关论文
共 52 条
  • [1] Nucleophilic aryloxydefluorination of pentafluorobenzene without noble metal catalysis
    Adonin, Nicolay Yu.
    Bardin, Vadim V.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 153 : 165 - 167
  • [2] Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines
    Altman, Ryan A.
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2007, 9 (04) : 643 - 646
  • [3] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers
    Aranyos, A
    Old, DW
    Kiyomori, A
    Wolfe, JP
    Sadighi, JP
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) : 4369 - 4378
  • [4] B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates
    Blackwell, JM
    Sonmor, ER
    Scoccitti, T
    Piers, WE
    [J]. ORGANIC LETTERS, 2000, 2 (24) : 3921 - 3923
  • [5] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione
    Buck, E
    Song, ZJ
    Tschaen, D
    Dormer, PG
    Volante, RP
    Reider, PJ
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1623 - 1626
  • [6] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects
    Burgos, Carlos H.
    Barder, Timothy E.
    Huang, Xiaohua
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4321 - 4326
  • [7] Polyfluorinated cycloalkoxyphenyl ether systems as dopants for liquid crystal display applications
    Cargill, Matthew R.
    Sandford, Graham
    Tomlinson, David J.
    Hollfelder, Nadine
    Pleis, Frank
    Nelles, Gabriele
    Kilickiran, Pinar
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2011, 132 (10) : 829 - 833
  • [8] O-Alkylation of phenol derivatives via a nucleophilic substitution
    Cazorla, Clement
    Pfordt, Emilie
    Duclos, Marie-Christine
    Metay, Estelle
    Lemaire, Marc
    [J]. GREEN CHEMISTRY, 2011, 13 (09) : 2482 - 2488
  • [9] Remarkably variable reaction modes of frustrated Lewis pairs with non-conjugated terminal diacetylenes
    Chen, Chao
    Froehlich, Roland
    Kehr, Gerald
    Erker, Gerhard
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (20) : 3580 - 3582
  • [10] Enantioselective Hydrosilylation with Chiral Frustrated Lewis Pairs
    Chen, Dianjun
    Leich, Valeri
    Pan, Fangfang
    Klankermayer, Juergen
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) : 5184 - 5187
123456