Role of the base and endogenous anions in "ligand-free" catalytic systems for the Suzuki-Miyaura reaction

被引:7
作者
Kurokhtina, A. A. [1 ]
Larina, E. V. [1 ]
Yarosh, E. V. [1 ]
Schmidt, A. F. [1 ]
机构
[1] Irkutsk State Univ, Fac Chem, Irkutsk 664003, Russia
关键词
Suzuki; Miyaura reaction; palladium; catalysis; base; CROSS-COUPLING REACTION; HECK REACTION; TRIPLE ROLE; PALLADIUM; COMPLEXES; TRANSMETALATION; IONS; NANOPARTICLES; INTERMEDIATE; MECHANISM;
D O I
10.1134/S0023158416030095
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
UV spectroscopic studies combined with kinetic measurements for the Suzuki-Miyaura reaction catalyzed by "ligand-free" catalytic systems have demonstrated that the base is involved in the formation of the palladium complexes ensuring the occurrence of the transmetalation stage. It follows from UV monitoring data for the catalytic reaction involving aryl iodides that a considerable part of palladium during the process is in the form of Pd2+ acid complexes with endogenous anions and does not participate in the main catalytic cycle.
引用
收藏
页码:373 / 379
页数:7
相关论文
共 28 条
  • [1] EVIDENCE FOR THE LIGATION OF PALLADIUM(0) COMPLEXES BY ACETATE IONS - CONSEQUENCES ON THE MECHANISM OF THEIR OXIDATIVE ADDITION WITH PHENYL IODIDE AND PHPD(OAC)(PPH(3))(2) AS INTERMEDIATE IN THE HECK REACTION
    AMATORE, C
    CARRE, E
    JUTAND, A
    MBARKI, MA
    MEYER, G
    [J]. ORGANOMETALLICS, 1995, 14 (12) : 5605 - 5614
  • [2] Mechanism of Palladium-Catalyzed Suzuki-Miyaura Reactions: Multiple and Antagonistic Roles of Anionic "Bases" and Their Countercations
    Amatore, Christian
    Le Duc, Gaetan
    Jutand, Anny
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (31) : 10082 - 10093
  • [3] The Triple Role of Fluoride Ions in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unprecedented Transmetalation from [ArPdFL2] Complexes
    Amatore, Christian
    Jutand, Anny
    Le Duc, Gaetan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) : 1379 - 1382
  • [4] Kinetic Data for the Transmetalation/Reductive Elimination in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unexpected Triple Role of Hydroxide Ions Used as Base
    Amatore, Christian
    Jutand, Anny
    Le Duc, Gaetan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2492 - 2503
  • [5] [Anonymous], 2008, ORGANOMETALLICS
  • [6] Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction
    Braga, AAC
    Morgon, NH
    Ujaque, G
    Maseras, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) : 9298 - 9307
  • [7] Computational study of the transmetalation process in the Suzuki-Miyaura cross-coupling of aryls
    Braga, Ataualpa A. C.
    Morgon, Nelson H.
    Ujaque, Gregori
    Lledos, Agusti
    Maseras, Feliu
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (21) : 4459 - 4466
  • [8] Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride
    Butters, Mike
    Harvey, Jeremy N.
    Jover, Jesus
    Lennox, Alastair J. J.
    Lloyd-Jones, Guy C.
    Murray, Paul M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) : 5156 - 5160
  • [9] Distinguishing Between Pathways for Transmetalation in Suzuki-Miyaura Reactions
    Carrow, Brad P.
    Hartwig, John F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) : 2116 - 2119
  • [10] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710