Synergistic Catalysis in the Sonogashira Coupling Reaction: Quantitative Kinetic Investigation of Transmetalation

被引:57
|
作者
He, Chuan [1 ]
Ke, Jie [1 ]
Xu, Huan [1 ]
Lei, Aiwen [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
cross-coupling; kinetics; reaction mechanisms; synergistic catalysis; transmetalation; DENSITY-FUNCTIONAL THEORY; REDUCTIVE ELIMINATION; STILLE REACTION; PALLADIUM; ARYL; MECHANISM; COPPER; CARBON; STEP; SUBSTITUENTS;
D O I
10.1002/anie.201207970
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Rate-limiting: The transmetalation step of the Sonogashira coupling reaction has been established as the rate-limiting step. This cross-coupling has been demonstrated to be a Pd-catalyzed and Cu-catalyzed synergistic process, which exhibits a first-order kinetic dependence on both the [Pd] and [Cu] catalysts (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1527 / 1530
页数:4
相关论文
共 50 条
  • [41] Recent progress and current applications of Sonogashira coupling reaction in water
    Bakherad, Mohammad
    APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) : 125 - 140
  • [42] Sonogashira coupling reaction with palladium powder and potassium fluoride in methanol
    Wang, L
    Li, PH
    CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (04) : 474 - 476
  • [43] Sonogashira Coupling Reaction with Palladium Powder and Potassium Fluoride in Methanol
    王磊
    李品华
    ChineseJournalofChemistry, 2003, (04) : 474 - 476
  • [44] Sonogashira coupling reaction with immobilized 4-halophenylboronic acids
    Pallares, G
    Perttu, EK
    Arnold, M
    Lovine, PM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U642 - U642
  • [45] The Sonogashira coupling reaction catalyzed by ultrafine nickel(0) powder
    Wang, L
    Li, PH
    Zhang, YC
    CHEMICAL COMMUNICATIONS, 2004, (05) : 514 - 515
  • [46] Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction
    Yamashita, Mitsuaki
    Ueda, Kazunori
    Sakaguchi, Koichi
    Iida, Akira
    TETRAHEDRON LETTERS, 2011, 52 (36) : 4665 - 4670
  • [47] KINETIC INVESTIGATION OF PEPTIDE COUPLING
    MUTTER, M
    HAGENMAIER, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (02) : 149 - 149
  • [48] Kinetic Strategies for the Formation of Graphyne Nanowires via Sonogashira Coupling on Ag(111)
    Zhu, Junfa (jfzhu@ustc.edu.cn), 1600, American Chemical Society (140):
  • [49] Kinetic Strategies for the Formation of Graphyne Nanowires via Sonogashira Coupling on Ag(111)
    Wang, Tao
    Huang, Jianmin
    Lv, Haifeng
    Fan, Qitang
    Feng, Lin
    Tao, Zhijie
    Ju, Huanxin
    Wu, Xiaojun
    Tait, Steven L.
    Zhu, Junfa
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (41) : 13421 - 13428
  • [50] Mechanochemistry in Senior Undergraduate Laboratory: NHC Complexes, Catalysis, and Sonogashira Cross-Coupling
    Shunnar, Abeer
    Rao, Ravulakollu Srinivasa
    Aslam, Mohamed
    Stephen, Sasi
    Al Saraierh, Hassan
    Lowe, Andrew B.
    Shaya, Janah
    JOURNAL OF CHEMICAL EDUCATION, 2025,