[Bmim]PF6-Promoted Ligandless Suzuki-Miyaura Coupling Reaction of Potassium Aryltrifluoroborates in Water

被引:37
|
作者
Liu, Leifang [1 ]
Dong, Yan [1 ]
Pang, Bo [1 ]
Ma, Jiahai [1 ]
机构
[1] Dezhou Univ, Key Lab Coordinat Chem & Funct Mat Univ Shandong, Dezhou 253023, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 15期
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED SUZUKI; TEMPERATURE IONIC LIQUIDS; ARYL CHLORIDES; AQUEOUS-MEDIA; ARYLBORONIC ACIDS; PHOSPHINE-LIGANDS; ORGANIC-SYNTHESIS; EFFICIENT; HALIDES; NANOPARTICLES;
D O I
10.1021/jo500840s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki-Miyaura coupling reactions of potassium aryltrifluoroborates with aryl bromides in water are promoted by the addition of [bmim]PF6 using Pd(OAc)(2) as a catalyst and Na2CO3 as a base under air. The quantity of [bmim]PF6 used is crucial to the efficiency of the catalytic system. A wide range of biaryls and polyaryls can be easily prepared in good to excellent yields.
引用
收藏
页码:7193 / 7198
页数:6
相关论文
共 50 条
  • [1] An Efficient Ligandless Palladium-catalyzed Protocol for Suzuki-Miyaura Coupling Reaction of Potassium Aryltrifluoroborates in Water
    Liu, Leifang
    Li, Mingcheng
    Yang, Jianhua
    Zhu, Baoyong
    Wang, Xinfang
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (20) : 2023 - 2028
  • [2] Palladium-catalyzed efficient Suzuki-Miyaura reaction of potassium aryltrifluoroborates in water
    Liu, Chun
    Li, Xinmin
    Wang, Xinnan
    Jin, Zilin
    CATALYSIS COMMUNICATIONS, 2015, 69 : 81 - 85
  • [3] An improved protocol for ligandless Suzuki-Miyaura coupling in water
    Korolev, Dmitrii N.
    Bumagin, Nikolay A.
    TETRAHEDRON LETTERS, 2006, 47 (25) : 4225 - 4229
  • [4] Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates
    Liu, Chun
    Liu, Chao
    Li, Xin-Min
    Gao, Zhan-Ming
    Jin, Zi-Lin
    CHINESE CHEMICAL LETTERS, 2016, 27 (05) : 631 - 634
  • [5] Microwave-accelerated Suzuki-Miyaura coupling reactions using potassium aryltrifluoroborates
    Harker, Rebecca L.
    Crouch, R. David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 545 - 545
  • [6] Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates
    Molander, Gary A.
    Elia, Maxwell D.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24): : 9198 - 9202
  • [7] Microwave-accelerated Suzuki-Miyaura coupling reactions using potassium aryltrifluoroborates
    Harker, Rebecca L.
    Crouch, R. David
    SYNTHESIS-STUTTGART, 2007, (01): : 25 - 27
  • [8] Synthesis of heterobiaryls via Suzuki-Miyaura coupling reaction of potassium aryltrifluoroborates with heteroaryl halides in aqueous systems
    Liu, Leifang
    Zhao, Kai
    Li, Wenbo
    Liu, Mingli
    Chen, Yuting
    Dong, Yan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
  • [9] A General Palladium Catalyst System for Suzuki-Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates
    Chow, Wing Kin
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5109 - 5112
  • [10] Oxygen-promoted Suzuki-Miyaura reaction of aryl fluorosulfates and potassium aryltrifluoroborates: Mild and efficient access to biaryls and terphenyls
    Li, Xinmin
    Ma, Yunhai
    Hu, Qinghong
    Jiang, Bo
    Wu, Qing
    Yuan, Zeli
    CATALYSIS COMMUNICATIONS, 2018, 117 : 57 - 62