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 110 条
  • [21] Microwave- and ultrasound-assisted Suzuki-Miyaura cross-coupling reactions catalyzed by Pd/PVP
    de Souza, Andrea Luzia F.
    da Silva, Lucyane C.
    Oliveira, Blanca L.
    Antunes, O. A. C.
    [J]. TETRAHEDRON LETTERS, 2008, 49 (24) : 3895 - 3898
  • [22] Synthesis of jaspaquinol and effect on viability of normal and malignant bladder epithelial cell lines
    Demotie, A
    Fairlamb, IJS
    Lu, FJ
    Shaw, NJ
    Spencer, PA
    Southgate, J
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (11) : 2883 - 2887
  • [23] Palladium-Catalyzed, Highly Efficient, Regiocontrolled Arylation of Electron-Rich Allylamines with Aryl Halides
    Deng, Yuheng
    Jiang, Zhen
    Yao, Min
    Xu, Dan
    Zhang, Lingjuan
    Li, Huanrong
    Tang, Weijun
    Xu, Lijin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (05) : 899 - 907
  • [24] Cross-Coupling of Aromatic Bromides with Allylic Silanolate Salts
    Denmark, Scott E.
    Werner, Nathan S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (48) : 16382 - 16393
  • [25] Regioselective Cross-Coupling of Allylboronic Acid Pinacol Ester Derivatives with Aryl Halides via Pd-PEPPSI-IPent
    Farmer, Jennifer L.
    Hunter, Howard N.
    Organ, Michael G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17470 - 17473
  • [26] Suzuki-Miyaura cross-coupling coupling reactions with low catalyst loading: a green and sustainable protocol in pure water
    Fihri, Aziz
    Luart, Denis
    Len, Christophe
    Solhy, Abderrahim
    Chevrin, Carole
    Polshettiwar, Vivek
    [J]. DALTON TRANSACTIONS, 2011, 40 (13) : 3116 - 3121
  • [27] Sulfonated N-heterocyclic carbenes for Suzuki coupling in water
    Fleckenstein, Christoph
    Roy, Sutapa
    Leuthaeusser, Steffen
    Plenio, Herbert
    [J]. CHEMICAL COMMUNICATIONS, 2007, (27) : 2870 - 2872
  • [28] Fleckenstein CA, 2007, GREEN CHEM, V9, P1287, DOI 10.1039/b711965h
  • [29] Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions-alternatives to PtBu3
    Fleckenstein, Christoph A.
    Plenio, Herbert
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) : 694 - 711
  • [30] Asymmetric synthesis of the fully functional macrolide core of salicylihalamide:: Remote control of olefin geometry during RCM
    Fürstner, A
    Thiel, OR
    Blanda, G
    [J]. ORGANIC LETTERS, 2000, 2 (23) : 3731 - 3734