Palladium-catalyzed direct arylation of polyfluoroarenes with aryl tosylates and mesylates

被引:37
|
作者
Lee, Dong Sheng [1 ,2 ,3 ,4 ]
Choy, Pui Ying [1 ,2 ,3 ]
So, Chau Ming [1 ,2 ,3 ]
Wang, Jun [1 ,2 ,3 ]
Lau, Chak Po [1 ,2 ,3 ]
Kwong, Fuk Yee [1 ,2 ,3 ]
机构
[1] State Key Lab Chirosci, Shenzhen, Peoples R China
[2] PolyU Shenzhen Res Inst SZRI, Shenzhen, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
[4] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan
来源
RSC ADVANCES | 2012年 / 2卷 / 24期
关键词
ELECTRON-DEFICIENT POLYFLUOROARENES; CROSS-COUPLING REACTIONS; C-H BONDS; MILD; AROMATICS; OXIDANT; ARENES; WATER;
D O I
10.1039/c2ra21667a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This study reports the first general Pd-catalyzed direct arylation of polyfluoroarenes with aryl tosylates/mesylates. A wide range of polyfluoroarenes can be coupled with both aryl tosylates and mesylates under relatively mild reaction conditions (90 degrees C, in the presence of a weak base KOAc, without any additional acid additives). Moreover, a one-pot sequential C-H bond functionalization/C-N bond coupling has been successfully accomplished by employing one single Pd/CM-phos catalyst system.
引用
收藏
页码:9179 / 9182
页数:4
相关论文
共 50 条
  • [21] Palladium-catalyzed direct arylation of polyfluoroarene and facile synthesis of liquid crystal compounds
    Ma, Xiaowei
    Liu, Yan
    Liu, Ping
    Xie, Jianwei
    Dai, Bin
    Liu, Zhiyong
    APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (03) : 180 - 185
  • [22] Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones
    Cao, Xiangxiang
    Bai, Yang
    Xie, Yanjun
    Deng, Guo-Jun
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2014, 383 : 94 - 100
  • [23] Palladium-Catalyzed Indole, Pyrrole, and Furan Arylation by Aryl Chlorides
    Nadres, Enrico T.
    Lazareva, Anna
    Daugulis, Olafs
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) : 471 - 483
  • [24] Palladium-Catalyzed Direct Arylation of 2-Pyridylmethyl Silanes with Aryl Bromides
    Lin, Tingzhi
    Qian, Pengcheng
    Wang, Yan-En
    Ou, Mingjie
    Jiang, Long
    Zhu, Chen
    Xu, Yuchuan
    Xiong, Dan
    Mao, Jianyou
    ORGANIC LETTERS, 2021, 23 (08) : 3000 - 3003
  • [25] Palladium-Catalyzed Olefination and Arylation of Polyfluoroarenes Using Molecular Oxygen as the Sole Oxidant
    Huang, Qiufeng
    Zhang, Xinyu
    Qiu, Lin
    Wu, Jiajun
    Xiao, Hanbing
    Zhang, Xiaofeng
    Lin, Shen
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3753 - 3757
  • [26] Exploiting Aryl Mesylates and Tosylates in Catalytic Mono-α-arylation of Aryl- and Heteroarylketones
    Fu, Wai Chung
    So, Chau Ming
    Yuen, On Ying
    Lee, Irene Toi Chuk
    Kwong, Fuk Yee
    ORGANIC LETTERS, 2016, 18 (08) : 1872 - 1875
  • [27] Palladium-Catalyzed Desulfitative Direct C-H Arylation of Electron-Deficient Polyfluoroarenes with Sodium Arenesulfinates
    Miao, Tao
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 429 - 436
  • [28] Preparation of fluorinated biaryls through direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates
    Fang, Xin
    Huang, Yuanyuan
    Chen, Xiaoqing
    Lin, Xiaoxi
    Bai, Zhengshuai
    Huang, Kuo-Wei
    Yuan, Yaofeng
    Weng, Zhiqiang
    JOURNAL OF FLUORINE CHEMISTRY, 2013, 151 : 50 - 57
  • [29] Thioethers as Directing Group for the Palladium-Catalyzed Direct Arylation of Arenes
    Yao, Jinzhong
    Yu, Ming
    Zhang, Yuhong
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (17) : 3205 - 3210
  • [30] Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes
    Ihanainen, Netta E.
    Kumpulainen, Esa T. T.
    Koskinen, Ari M. P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (15) : 3226 - 3229