Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

被引：27
|
作者：
Duesel, Simon Josef Siegfried [1 ]
Koenig, Burkhard [1 ]
机构：
[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 10期
关键词：
Chlorination; Photoredox catalysis; Oxidation; ipso-Substitution; Green chemistry; CHLORINATION; CHEMISTRY; CHLORIDE; ALKYNES; SUBSTITUTION; HALOGENATION; ACTIVATION; CATALYSIS; EFFICIENT; ALPHA;
D O I：
10.1002/ejoc.201900411
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.
引用
收藏
页码：1491 / 1495
页数：5
相关论文
共 50 条
  • [1] Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone
    Petzold, Daniel
    Koenig, Burkhard
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 626 - 630
  • [2] Photocatalytic Oxidative Iodination of Electron-Rich Arenes
    Narobe, Rok
    Dusel, Simon J. S.
    Iskra, Jernej
    Konig, Burkhard
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 3998 - 4004
  • [3] Highly Efficient and Practical Oxidative Bromination of Electron-Rich Arenes Using S-Methyl Methanethiosulfonate as the Oxidant
    Wang, Shaolong
    Zhou, Yong
    Wang, Jianbo
    Li, Ruolan
    Huang, Chaoqun
    Pang, Huailin
    Li, Xun
    SYNLETT, 2025, 36 (01) : 87 - 91
  • [4] Synthesis of Pterocarpan-Type Heterocycles via Oxidative Cycloadditions of Phenols and Electron-Rich Arenes
    Mohr, Amber L.
    Lombardo, Vincent M.
    Arisco, Teresa M.
    Morrow, Gary W.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (21) : 3845 - 3855
  • [5] Direct oxidative coupling of electron-rich arenes via double C-H functionalization
    Dwight, Timothy A.
    DeBoef, Brenton
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [6] Radiofluorination of Electron-Rich Arenes via LED-Promoted Photoredox Reactions
    Wang, Li
    Chen, Wei
    Wu, Zhanhong
    Nicewicz, David
    Li, Zibo
    JOURNAL OF NUCLEAR MEDICINE, 2021, 62
  • [7] Iodine pentoxide-mediated oxidative selenation and seleno/thiocyanation of electron-rich arenes
    Wang, Yong-Hao
    Zhang, Yun-Qian
    Zhou, Chen-Fan
    Jiang, You-Qin
    Xu, Yue
    Zeng, Xiaobao
    Liu, Gong-Qing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (27) : 5463 - 5469
  • [8] Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes
    Caramenti, Paola
    Nandi, Raj Kumar
    Waser, Jerome
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (40) : 10049 - 10053
  • [9] Electrochemical Hydroxylation of Electron-Rich Arenes in Continuous Flow
    Kooli, Anni
    Wesenberg, Lars
    Beslac, Marko
    Krech, Anastasiya
    Lopp, Margus
    Noel, Timothy
    Oseka, Maksim
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (20)
  • [10] Solvent-free nitration of electron-rich arenes
    Jagadish, Bhumasamudram
    Hurley, Nathaniel R.
    Mash, Eugene A.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (24) : 2395 - 2398
12345