Suzuki-Miyaura Reactions Catalyzed by C2-Symmetric Pd-Multi-Dentate N-Heterocyclic Carbene Complexes

被引：13
|
作者：
Jiang, Lan [1 ,2 ]
Shan, Fengjun [2 ]
Li, Zhengning [2 ]
Zhao, Defeng [1 ]
机构：
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Dalian Univ, Coll Environm & Chem Engn, Dalian 116622, Peoples R China
来源：
MOLECULES | 2012年 / 17卷 / 10期
关键词：
imidazolium salt; N-heterocyclic carbene; palladium; Suzuki-Miyaura coupling; catalysis; CROSS-COUPLING REACTIONS; ARYL CHLORIDES; PALLADIUM(II) COMPLEXES; HIGHLY EFFICIENT; ATOM-EFFICIENT; HECK; NHC; LIGANDS; BROMIDES; HALIDES;
D O I：
10.3390/molecules171012121
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Suzuki-Miyaura coupling reactions are promoted by Pd complexes ligated with C-2-symmetric multi-dentate N-heterocyclic carbenes derived in situ from Pd(OAc)(2) and imidazolium salts. Good to excellent yields were obtained for aryl bromides as substrates. Turnover numbers of up to 10(5) could be achieved with 5 x 10(-4) mol% of Pd(OAc)(2)/1 x 10(-3) mol% NHC precatalyst in 24 h.
引用
收藏
页码：12121 / 12139
页数：19
相关论文
共 50 条
  • [41] Phosphine/N-heterocyclic carbene palladium complex for Suzuki-Miyaura cross-coupling reactions: The role of water on activity
    Lahneche, Youssra Doria
    Lachguar, Abdelhak
    Mouton, Clement
    Daran, Jean-Claude
    Manoury, Eric
    Poli, Rinaldo
    Benslimane, Meriem
    Labande, Agnes
    Deydier, Eric
    INORGANICA CHIMICA ACTA, 2019, 492 : 91 - 97
  • [42] Palladium(II)-N-Heterocyclic Carbene Metallacrown Ether Complexes: Synthesis, Structure, and Catalytic Activity in the Suzuki-Miyaura Reaction
    Zhang, Xiaoqin
    Qiu, Yuping
    Rao, Bin
    Luo, Meiming
    ORGANOMETALLICS, 2009, 28 (10) : 3093 - 3099
  • [43] Triazole-Functionalized N-Heterocyclic Carbene Complexes of Palladium and Platinum and Efficient Aqueous Suzuki-Miyaura Coupling Reaction
    Gu, Shaojin
    Xu, Hui
    Zhang, Na
    Chen, Wanzhi
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (07) : 1677 - 1686
  • [44] Nickel(ii) N-heterocyclic carbene complexes as efficient catalysts for the Suzuki—Miyaura reaction
    S. B. Soliev
    A. V. Astakhov
    D. V. Pasyukov
    V. M. Chernyshev
    Russian Chemical Bulletin, 2020, 69 : 683 - 690
  • [45] Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids
    Albright, Abigail
    Eddings, Daniel
    Black, Regina
    Welch, Christopher J.
    Gerasimchuk, Nikolay N.
    Gawley, Robert E.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7341 - 7351
  • [46] Aqueous-Phase Chemistry of η3-Allylpalladium(II) Complexes with Sulfonated N-Heterocyclic Carbene Ligands: Solvent Effects in the Protolysis of Pd-C Bonds and Suzuki-Miyaura Reactions
    Asensio, Juan M.
    Andres, Roman
    Gomez-Sal, Pilar
    de Jesus, Ernesto
    ORGANOMETALLICS, 2017, 36 (21) : 4191 - 4201
  • [47] Syntheses of Novel C2-Symmetric Chiral Bidentate Bis(N-heterocyclic carbene) Ligands and Their Molybdenum Complexes
    Anezaki, Satoshi
    Yamaguchi, Yoshitaka
    Asami, Masatoshi
    CHEMISTRY LETTERS, 2010, 39 (04) : 398 - 399
  • [48] NHC-Pd(II)-Im (NHC = N-heterocyclic carbene; Im=1-methylimidazole) complexes as efficient catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides
    Tang, Yi-Qiang
    Lu, Jian-Mei
    Shao, Li-Xiong
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (23) : 3741 - 3744
  • [49] Highly effective silica gel-supported N-heterocyclic carbene-Pd catalyst for Suzuki-Miyaura coupling reaction
    Qiu, Huili
    Sarkar, Shaheen M.
    Lee, Dong-Hwan
    Jin, Myung-Jong
    GREEN CHEMISTRY, 2008, 10 (01) : 37 - 40
  • [50] Facile Suzuki-Miyaura cross coupling using ferrocene tethered N-heterocyclic carbene-Pd complex anchored on cellulose
    Kale, Dolly
    Rashinkar, Gajanan
    Kumbhar, Arjun
    Salunkhe, Rajashri
    REACTIVE & FUNCTIONAL POLYMERS, 2017, 116 : 9 - 16
12345