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
  • [1] Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media
    Alacid, Emilio
    Najera, Carmen
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (11) : 1658 - 1665
  • [2] Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5588 - 5594
  • [3] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction
    Alonso, Francisco
    Beletskaya, Irina P.
    Yus, Miguel
    [J]. TETRAHEDRON, 2008, 64 (14) : 3047 - 3101
  • [4] Selective Cross-Coupling of Organic Halides with Allylic Acetates
    Anka-Lufford, Lukiana L.
    Prinsell, Michael R.
    Weix, Daniel J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 9989 - 10000
  • [5] Highly effective alternative aryl trihydroxyborate salts for a ligand-free, on-water Suzuki-Miyaura coupling reaction
    Basu, Basudeb
    Biswas, Kinkar
    Kundu, Sekhar
    Ghosh, Sujit
    [J]. GREEN CHEMISTRY, 2010, 12 (10) : 1734 - 1738
  • [6] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
    Bellina, F
    Carpita, A
    Rossi, R
    [J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
  • [7] Application of Sharpless asymmetric dihydroxylation to thienyl-and benzothienyl acrylates and crotonates
    Bonini, Carlo
    Chiummiento, Lucia
    De Bonis, Margherita
    Funicello, Maria
    Lupattelli, Paolo
    Pandolfo, Rocco
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2919 - 2924
  • [8] Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles
    Botella, L
    Nájera, C
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 663 (1-2) : 46 - 57
  • [9] Bouyssi D, 2002, EUR J ORG CHEM, V2002, P2445
  • [10] A convenient preparation of 4-iodoindoles from indoles: application to the chemical synthesis of hapalindole alkaloids
    Brown, MA
    Kerr, MA
    [J]. TETRAHEDRON LETTERS, 2001, 42 (06) : 983 - 985