Unsymmetric-1,3-disubstituted imidazolium salt for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl bromides

被引:23
|
作者
Yu, HW
Shi, JC [1 ]
Zhang, H
Yang, PY
Wang, XP
Jin, ZL
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
基金
中国国家自然科学基金;
关键词
palladium; imidazol-2-ylidene; Suzuki-Miyaura reaction; aryl bromides; catalysis;
D O I
10.1016/j.molcata.2006.01.034
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of 1-(ferrocenylethyl)-3-substituted-imidazolium salts [3-substitute=2,6-di(iso-propyl)phenyl (1a), 2,4,6-trimethylphenyl (1b), tertbutyl (1c), I-Ad (1d), cyclohexyl (1e)] have been synthesized from a racemic ferrocertylethyl acetate and the corresponding N-substituted imidazole in high yields (70-94%). A combination of Pd(OAc)(2) and 1a-d was found to form an excellent catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl bromides with phenylboronic acid in the presence of Cs2CO3 (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:15 / 19
页数:5
相关论文
共 50 条
  • [21] Cycloheptatrienyl Cyclopentadienyl Titanium Phosphane Ligands in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions
    Troendle, Sabrina
    Kuate, Alain C. Tagne
    Freytag, Matthias
    Jones, Peter G.
    Tamm, Matthias
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (47) : 5588 - 5597
  • [22] Carbon monoxide surrogates for palladium-catalyzed Suzuki-Miyaura and Sonogashira carbonylative cross-coupling reactions
    Aronica, Laura Antonella
    INORGANICA CHIMICA ACTA, 2023, 558
  • [23] A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8059 - 8063
  • [24] Efficient salicylaldimine ligands for a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
    Liu, Feng-Shou
    Huang, Ying-Tang
    Lu, Chao
    Shen, Dong-Sheng
    Cheng, Tao
    APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (08) : 425 - 429
  • [25] Stereoselective Preparation and Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkenyl Sulfoximines
    Yasui, Kosuke
    Tomishima, Yuichiro
    Miura, Tomoya
    Yamazaki, Ken
    Hirano, Koji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (11)
  • [26] Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki-Miyaura Cross-Coupling of Allylboronates and Aryl Halides
    Yang, Yang
    Buchwald, Stephen L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) : 10642 - 10645
  • [27] Palladium-catalyzed Buchwald-Hartwig Amination and Suzuki-Miyaura Cross-coupling Reaction of Aryl Mesylates
    Wong, Shun Man
    Choy, Pui Ying
    Yuen, On Ying
    So, Chau Ming
    Kwong, Fuk Yee
    ORGANIC SYNTHESES, 2015, 92 : 195 - +
  • [28] Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)benzyl Tosylates
    Brambilla, Marta
    Tredwell, Matthew
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) : 11981 - 11985
  • [29] The Origin of Shape Sensitivity in Palladium-Catalyzed Suzuki-Miyaura Cross Coupling Reactions
    Collins, Gillian
    Schmidt, Michael
    Dwyer, Colm O.
    Holmes, Justin D.
    McGlacken, Gerard P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4142 - 4145
  • [30] Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling
    Andrus, MB
    Song, C
    ORGANIC LETTERS, 2001, 3 (23) : 3761 - 3764