Nitrosonium Ion Catalyzed Oxidative Bromination of Arenes

被引:2
|
作者
Chen, Pin-Hsien [1 ]
Hsu, Shu-Jung [1 ]
Hou, Duen-Ren [1 ]
机构
[1] Natl Cent Univ, Dept Chem, 300 Jhong Da Rd, Taoyuan 320317, Taiwan
关键词
nitrosonium; bromination; arene; metal-free reaction; ESTROGEN-RECEPTOR MODULATOR; ELECTRON-TRANSFER; AROMATIC BROMINATION; ARYL; HALOGENATION; NITROSATION; CONVENIENT; NITRATION; EFFICIENT; BROMIDE;
D O I
10.1002/adsc.202301200
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A nitrosonium catalyzed bromination of electron-rich arenes has been developed, using bromide salts as bromine sources, oxygen gas as a terminal oxidant and Bronsted acids (sulfuric acid, TFA or HBr). This arene bromination process is free of transition metals, proceeding in acetic acid and under mild temperatures (25-50 degrees C) to give brominated arenes with good to excellent yields. Our mechanistic studies indicated that this oxidative bromination of arenes reaction is catalyzed by nitrosnium ion (NO+), without the involvement of Br2 or Br+. The kinetic isotope effect of this reaction was measured using pentadeuteriophenyl phenyl ether (kH/kD=1.1). image
引用
收藏
页码:1575 / 1582
页数:8
相关论文
共 50 条
  • [1] Recent progress in the oxidative bromination of arenes and heteroarenes
    Jiang, Da-Bo
    Wu, Fei-Yue
    Cui, Hai-Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (08) : 1571 - 1590
  • [2] OXIDATIVE AROMATIC NITRATION WITH CHARGE-TRANSFER COMPLEXES OF ARENES AND NITROSONIUM SALTS
    KIM, EK
    KOCHI, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07): : 1692 - 1702
  • [3] Efficient Pd-Catalyzed C-H Oxidative Bromination of Arenes with Dimethyl Sulfoxide and Hydrobromic Acid
    Yuan, Yizhi
    Liang, Yujie
    Shi, Shihui
    Liang, Yu-Feng
    Jiao, Ning
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) : 1245 - 1251
  • [4] Nitrosation of arenes with nitrosonium ethyl sulfate
    N. V. Zyk
    E. E. Nesterov
    A. N. Khlobystov
    N. S. Zefirov
    Russian Chemical Bulletin, 1999, 48 : 506 - 509
  • [5] Nitrosation of arenes with nitrosonium ethyl sulfate
    Zyk, NV
    Nesterov, EE
    Khlobystov, AN
    Zefirov, NS
    RUSSIAN CHEMICAL BULLETIN, 1999, 48 (03) : 506 - 509
  • [6] Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination
    Duesel, Simon Josef Siegfried
    Koenig, Burkhard
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1491 - 1495
  • [7] Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone
    Petzold, Daniel
    Koenig, Burkhard
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 626 - 630
  • [8] Gold-Catalyzed Oxidative Acyloxylation of Arenes
    Zanda, Matteo
    SYNLETT, 2012, (04) : A26 - A27
  • [9] Gold-Catalyzed Oxidative Acyloxylation of Arenes
    Pradal, Alexandre
    Toullec, Patrick Y.
    Michelet, Veronique
    ORGANIC LETTERS, 2011, 13 (22) : 6086 - 6089
  • [10] Ni(II)-Catalyzed Oxidative Coupling of Arenes
    Wu, Jieqing
    Gu, Jiefan
    Chen, Qinrui
    Ma, Hongfei
    Li, Yufeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2772 - 2777