An Efficient Method for Sterically Demanding Suzuki-Miyaura Coupling Reactions

被引:100
作者
Zhao, Qing [1 ]
Li, Chengxi [1 ]
Senanayake, Chris H. [2 ]
Tang, Wenjun [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Beijing 100864, Peoples R China
[2] Boehringer Ingelheim Pharmaceut Inc, Chem Dev, Ridgefield, CT 06877 USA
关键词
biaryls; cross-coupling; homogeneous catalysis; palladium; steric hindrance; ORTHO-SUBSTITUTED BIARYLS; HETEROCYCLIC CARBENE COMPLEXES; HINDERED ARYL CHLORIDES; GENERAL-METHOD; CATALYST; LIGAND; NHC; RUTHENOCENYLPHOSPHINE; HALIDES; BINOL;
D O I
10.1002/chem.201203898
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for sterically demanding Suzuki-Miyaura coupling reactions has been developed with two catalysts, Pd/BI-DIME (see scheme) and Pd/phenanthrene-based ligand. The Pd/BI-DIME catalyst facilitates the syntheses of extremely hindered biaryls bearing ortho-isopropyl substituents. The other catalyst is efficient for the synthesis of functionalized tetra-ortho- substituted biaryls at low catalyst loadings. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2261 / 2265
页数:5
相关论文
共 50 条
  • [41] Recent Progress in the Suzuki-Miyaura Cross-Coupling Reactions in Water
    Xu, Peng
    Duan, Xinhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3315 - 3327
  • [42] The Slow-Release Strategy in Suzuki-Miyaura Coupling
    Lennox, Alastair J. J.
    Lloyd-Jones, Guy C.
    ISRAEL JOURNAL OF CHEMISTRY, 2010, 50 (5-6) : 664 - 674
  • [43] Site-Selective Arylation of Alizarin and Purpurin Based on Suzuki-Miyaura Cross-Coupling Reactions
    Mahal, Ahmed
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (11) : 2075 - 2087
  • [44] Mercaptoaryl-Oxazoline Complexes of Palladium and Their High Activities as Catalysts for Suzuki-Miyaura Coupling Reactions in Water
    Holzer, Christof
    Dupe, Antoine
    Peschel, Lydia M.
    Belaj, Ferdinand
    Moesch-Zanetti, Nadia C.
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (05) : 568 - 575
  • [45] Caffeine and theophylline as sustainable, biosourced NHC ligand precursors for efficient palladium-catalyzed Suzuki-Miyaura cross-coupling reactions
    Mazars, Francois
    Zaragoza, Guillermo
    Delaude, Lionel
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2022, 978
  • [46] Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki-Miyaura Coupling Reactions
    Benhamou, Laure
    Besnard, Celine
    Kuendig, E. Peter
    ORGANOMETALLICS, 2014, 33 (01) : 260 - 266
  • [47] "Naked Nickel"-Catalyzed Heteroaryl-Heteroaryl Suzuki-Miyaura Coupling
    Saeb, Rakan
    Roh, Byeongdo
    Cornella, Josep
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [48] Palladium-catalysed Suzuki-Miyaura coupling reactions of Bromhexine and Ambroxol
    Sharif, Muhammad
    Pews-Davtyan, Anahit
    Lukas, Jan
    Pohlers, Susann
    Rolfs, Arndt
    Langer, Peter
    Beller, Matthias
    TETRAHEDRON, 2014, 70 (34) : 5128 - 5135
  • [49] An Efficient Suzuki-Miyaura Coupling of Aryl Sulfamates and Boronic Acids Catalyzed by NiCl2(dppp)
    Chen, Guo-Jun
    Han, Fu-She
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) : 3575 - 3579
  • [50] Iron-Catalyzed Alkyl-Alkyl Suzuki-Miyaura Coupling
    Hatakeyama, Takuji
    Hashimoto, Toru
    Kathriarachchi, Kalum K. A. D. S.
    Zenmyo, Takeshi
    Seike, Hirofumi
    Nakamura, Masaharu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (35) : 8834 - 8837