Pd-catalyzed ligand-free Suzuki reaction of β-substituted allylic halides with arylboronic acids in water

被引:15
|
作者
Dong, Chaonan [1 ]
Zhang, Lingjuan [1 ]
Xue, Xiao [1 ]
Li, Huanrong [1 ]
Yu, Zhiyong [1 ]
Tang, Weijun [1 ]
Xu, Lijin [1 ]
机构
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
来源
RSC ADVANCES | 2014年 / 4卷 / 22期
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; BAYLIS-HILLMAN ADDUCTS; AQUEOUS-MEDIA; ARYL HALIDES; PALLADIUM CATALYSTS; MIYAURA COUPLINGS; BORONIC ACIDS; SUPPORTED PALLADIUM; REUSABLE CATALYST; HIGHLY EFFICIENT;
D O I
10.1039/c3ra47813k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalyst system consisting of Pd(TFA)(2) and KOH allows for a wide range of beta-substituted allylic halides to react efficiently with various arylboronic acids in neat water under ligand-free conditions, affording the allylated arenes in high yields with broad functional group tolerance and up to 7.4 x 10(5) TON and 15 416 h(-1) TOF.
引用
收藏
页码:11152 / 11158
页数:7
相关论文
共 50 条
  • [41] Pd-Catalyzed Asymmetric Addition of Arylboronic Acids to Pyrazolinone Ketimines
    Miao, An-Qi
    Zhou, Meng
    Chen, Jing-Long
    Wang, Shi-Chao
    Hao, Wen-Juan
    Tu, Shu-Jiang
    Jiang, Bo
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (22) : 5162 - 5166
  • [42] Bio-surfactant: a green and environmentally benign reaction medium for ligand-free Pd-catalyzed Mizoroki–Heck cross-coupling reaction in water
    Seema P. Patil
    Sanjay N. Jadhav
    Chandrashekhar V. Rode
    Rajendra V. Shejwal
    Arjun S. Kumbhar
    Transition Metal Chemistry, 2020, 45 : 403 - 411
  • [43] Pd-catalyzed Suzuki cross-coupling reactions of glycerol arylboronic esters
    Nichele, Tatiana Z.
    Favero, Cristiano
    Monteiro, Adriano L.
    CATALYSIS COMMUNICATIONS, 2009, 10 (05) : 693 - 696
  • [44] Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates
    Xu, Zhenli
    Zhang, Zongxue
    Meng, Chenxiang
    Zhang, Xiaoya
    Xu, Kai
    Liu, Lantao
    Wang, Tao
    Xu, Haiyun
    Mao, Guoliang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3264 - 3271
  • [45] Ligand-Free Palladium-Catalyzed Aerobic Oxidative Coupling of Carboxylic Anhydrides with Arylboronic Acids
    Yin, Weiyan
    He, Haifeng
    Zhang, Yani
    Long, Tong
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2402 - 2406
  • [46] Pd/C Catalyzed Suzuki-Miyaura Coupling Reaction of Arylboronic Acids with Triarylantimony Diacetatcs
    Xin, Zhuo
    Wu, Xiaoli
    Huang, Yuxing
    Ma, Yongqiang
    Zhao, Shouyuan
    Wang, Qian
    Jin, Zhong
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2012, 34 (02): : 433 - 435
  • [47] An Aerobic and Very Fast Pd/C-Catalyzed Ligand-Free and Aqueous Suzuki Reaction Under Mild Conditions
    Liu, Chun
    Rao, Xiaofeng
    Zhang, Yixia
    Li, Xinmin
    Qiu, Jieshan
    Jin, Zilin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4345 - 4350
  • [48] Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of (hetero)aryl-substituted triphenylamine derivatives
    Liu, Chun
    Rao, Xiaofeng
    Song, Xinlong
    Qiu, Jieshan
    Jin, Zilin
    RSC ADVANCES, 2013, 3 (02): : 526 - 531
  • [49] Chemically Modified Chitosan Supports for Phosphine-free Pd-catalyzed Crosscoupling Reaction of Arylboronic Acids with Acid Chlorides
    Kong, Hyoung-Jun
    Bang, Do-Won
    Kim, Minji
    Park, Soo-Youl
    Kim, Seung-Hoi
    CURRENT ORGANIC CHEMISTRY, 2022, 26 (04) : 418 - 425
  • [50] Ligand-free Suzuki-Miyaura reaction catalysed by Pd/C at room temperature
    Zhang, GL
    JOURNAL OF CHEMICAL RESEARCH, 2004, (09) : 593 - 595