Proline Catalyzes Direct C-H Arylations of Unactivated Arenes

被引:94
|
作者
Tanimoro, Kouichi [1 ]
Ueno, Minoru [1 ]
Takeda, Kazutaka [1 ]
Kirihata, Mitsunori [1 ]
Tanimori, Shinji [1 ]
机构
[1] Osaka Prefecture Univ, Grad Sch Life & Environm Sci, Dept Biosci & Informat, Naka Ku, 1-1 Gakuencho, Sakai, Osaka 5998531, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 18期
关键词
CROSS-COUPLING REACTIONS; BOND ARYLATION; SELF-ORGANIZATION; ROOM-TEMPERATURE; ARYL HALIDES; ORGANOCATALYSIS; HETEROCYCLES; ACTIVATION; BENZENE; INDOLES;
D O I
10.1021/jo3008594
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several amino acids were tested to catalyze the transition-metal-free direct C-H arylation of unactivated benzene derivatives. Among them, proline was found to be an excellent catalyst for the cross-coupling between aryl halides and unactivated arenes. The reaction presumably involves an aryl radical anion as the intermediate based on several experiments. The reaction using this catalyst system offers an option toward establishing an environmentally benign and cost-effective route to biaryls.
引用
收藏
页码:7844 / 7849
页数:6
相关论文
共 50 条
  • [31] Polyfunctional Conjugated Microporous Polymers for Applications in Direct C-H Arylation of Unactivated Arenes and Aqueous Adsorption of Aromatic Amines
    Luo Kexin
    Su Qing
    Ju Pengyao
    Li Xiaodong
    Liu Ziqian
    Sun Xiaoman
    Li Guanghua
    Wu Qiaolin
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2020, 36 (06) : 1302 - 1309
  • [32] Polyfunctional Conjugated Microporous Polymers for Applications in Direct C-H Arylation of Unactivated Arenes and Aqueous Adsorption of Aromatic Amines
    Kexin Luo
    Qing Su
    Pengyao Ju
    Xiaodong Li
    Ziqian Liu
    Xiaoman Sun
    Guanghua Li
    Qiaolin Wu
    Chemical Research in Chinese Universities, 2020, 36 : 1302 - 1309
  • [33] Mixed Directing-Group Strategy: Oxidative C-H/C-H Bond Arylation of Unactivated Arenes by Cobalt Catalysis
    Du, Cong
    Li, Peng-Xiang
    Zhu, Xinju
    Suo, Jian-Feng
    Niu, Jun-Long
    Song, Mao-Ping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (43) : 13571 - 13575
  • [34] Cobalt-Catalyzed Aerobic Oxidative C-H/C-H Cross-Coupling of Unactivated Arenes for the Synthesis of Biaryls
    Lv, Ningning
    Chen, Zhengkai
    Liu, Yue
    Liu, Zhanxiang
    Zhang, Yuhong
    ORGANIC LETTERS, 2018, 20 (18) : 5845 - 5848
  • [35] Ruthenium-Catalyzed Direct Arylations Through C-H Bond Cleavages
    Ackermann, Lutz
    Vicente, Ruben
    C-H ACTIVATION, 2010, 292 : 211 - 229
  • [36] Direct arylation via cleavage of activated and unactivated C-H bonds
    Miura, M
    Nomura, M
    CROSS-COUPLING REACTIONS: A PRACTICAL GUIDE, 2002, 219 : 211 - 241
  • [37] Iron-mediated C-H coupling of arenes and unactivated terminal alkenes directed by sulfur
    Cavanagh, Craig W.
    Aukland, Miles H.
    Hennessy, Alan
    Procter, David J.
    CHEMICAL COMMUNICATIONS, 2015, 51 (45) : 9272 - 9275
  • [38] Oxidation of unactivated C-H bonds
    Loredo, Leticia
    Perera, Roshan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [39] Sustainable protocols for direct C-H bond arylation of (hetero)arenes
    Albano, Gianluigi
    Punzi, Angela
    Capozzi, Maria Annunziata M.
    Farinola, Gianluca M.
    GREEN CHEMISTRY, 2022, 24 (05) : 1809 - 1894
  • [40] Transition Metals Catalyzed Direct C-H Chalcogentaion of Arenes and Heteroarenes
    Mahata, Atanu
    Garain, Madhusudan
    Roy, Totan
    Gorai, Dilip
    Kundu, Debasish
    CURRENT ORGANIC SYNTHESIS, 2024, 21 (06) : 764 - 795