A Mild Palladium-Catalyzed Suzuki Coupling Reaction of Quinoline Carboxylates with Boronic Acids

被引:17
|
作者
Li, Wenjie [1 ]
Gao, Joe J. [1 ]
Zhang, Yongda [1 ]
Tang, Wenjun [1 ]
Lee, Heewon [1 ]
Fandrick, Keith R. [1 ]
Lu, Bruce [1 ]
Senanayake, Chris H. [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Ridgefield, CT 06877 USA
关键词
monophosphanes; palladium; quinolines; room temperature reaction; Suzuki-Miyaura cross-coupling; ARYL CHLORIDES; ROOM-TEMPERATURE; SUBSTITUTED QUINOLINES; ORGANOBORON COMPOUNDS; ARYLBORONIC ACIDS; FACILE SYNTHESIS; DERIVATIVES; ARENESULFONATES; ELECTROPHILES; CYCLIZATION;
D O I
10.1002/adsc.201100141
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A palladium-catalyzed cross-coupling between aryl carboxylates and boronic acids has been achieved for the first time by taking advantage of the enhanced reactivity of quinoline 4-carboxylates. Also for the first time a Suzuki coupling reaction via a self-activation of boronic acids without addition of base is described. The reactions proceed under mild conditions (25-65 degrees C) to give excellent yields, and a wide range of functionalities is tolerated.
引用
收藏
页码:1671 / 1675
页数:5
相关论文
共 50 条
  • [41] Nickel-promoted ligand-free palladium-catalyzed Suzuki coupling reaction
    Wei Wang
    Rongliang Wang
    Fan Wu
    Boshun Wan
    Reaction Kinetics and Catalysis Letters, 2005, 85 : 277 - 282
  • [42] Enantioselective Dicarbofunctionalization of Unactivated Alkenes by Palladium-Catalyzed Tandem Heck/Suzuki Coupling Reaction
    Zhang, Zhan-Ming
    Xu, Bing
    Wu, Lizuo
    Wu, Yuanqi
    Qian, Yanyan
    Zhou, Lujia
    Liu, Yu
    Zhang, Junliang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (41) : 14653 - 14659
  • [43] Nickel-promoted ligand-free palladium-catalyzed Suzuki coupling reaction
    Wang, W
    Wang, RL
    Wu, F
    Wan, BS
    REACTION KINETICS AND CATALYSIS LETTERS, 2005, 85 (02): : 277 - 282
  • [44] Palladium-catalyzed cross-coupling reactions of paramagnetic vinyl bromides and paramagnetic boronic acids
    Kálai, T
    Jekö, J
    Berente, Z
    Hideg, K
    SYNTHESIS-STUTTGART, 2006, 3 (03): : 439 - 446
  • [45] Palladium-Catalyzed Aminocarbonylation of N-Chloroamines with Boronic Acids
    Li, Wanfang
    Wu, Xiao-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (20) : 7374 - 7378
  • [46] A simple and practical protocol for the palladium-catalyzed cross-coupling of boronic acids with methyl iodide
    Goossen, LJ
    APPLIED ORGANOMETALLIC CHEMISTRY, 2004, 18 (11) : 602 - 604
  • [47] Unsymmetrical diaryl Sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides
    Bandgar, BP
    Bettigeri, SV
    Phopase, J
    ORGANIC LETTERS, 2004, 6 (13) : 2105 - 2108
  • [48] Palladium-catalyzed homo-coupling of boronic acids with supported reagents in supercritical carbon dioxide
    Lei Zhou Qiu Xiang Xu Huan Feng Jiang College of Chemistry
    ChineseChemicalLetters, 2007, (09) : 1043 - 1046
  • [49] Palladium-catalyzed homo-coupling of boronic acids with supported reagents in supercritical carbon dioxide
    Zhou, Lei
    Xu, Qiu Xiang
    Jiang, Huan Feng
    CHINESE CHEMICAL LETTERS, 2007, 18 (09) : 1043 - 1046
  • [50] Palladium catalyzed ligand-free Suzuki cross-coupling reactions of benzylic halides with aryl boronic acids under mild conditions
    Bandgar, BP
    Bettigeri, SV
    Phopase, J
    TETRAHEDRON LETTERS, 2004, 45 (37) : 6959 - 6962