"Dba-free" palladium intermediates of the Heck-Matsuda reaction

被引:26
|
作者
Machado, Angelo H. L. [1 ]
Milagre, Humberto M. S. [2 ,3 ]
Eberlin, Livia S. [2 ]
Sabino, Adao A. [2 ,4 ]
Correia, Carlos Roque D. [1 ]
Eberlin, Marcos N. [2 ]
机构
[1] Univ Campinas UNICAMP, Inst Chem, Campinas, Brazil
[2] Univ Campinas UNICAMP, Thomson Lab, Campinas, Brazil
[3] Univ Estadual Paulista UNESP, Inst Biosci, Rio Claro, Brazil
[4] Univ Fed Minas Gerais, Dept Chem, Belo Horizonte, MG, Brazil
关键词
IONIZATION MASS-SPECTROMETRY; CROSS-COUPLING REACTIONS; ESI-MS; GAS-PHASE; REACTION-MECHANISMS; DIAZONIUM SALTS; ARYLATION; LIGANDS; SUZUKI; DERIVATIVES;
D O I
10.1039/c3ob40142a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The "dba-free" Heck-Matsuda reaction was investigated via direct ESI-MS(/MS) monitoring. Palladium species involved in the reduction of Pd(II) during a Wacker type reaction and several "dba-free" arylpalladium transient complexes were detected and characterized. Based on these findings, a more comprehensible catalytic cycle for this pivotal reaction is suggested.
引用
收藏
页码:3277 / 3281
页数:5
相关论文
共 50 条
  • [1] Heck-Matsuda Reaction Catalyzed by Heterogeneous Palladium Catalysts
    Oger, Nicolas
    Le Grognec, Erwan
    Felpin, Francois-Xavier
    CURRENT ORGANIC CHEMISTRY, 2015, 19 (08) : 695 - 707
  • [2] Heck-Matsuda reaction of arenediazonium salts in water
    Salabert, Jordi
    Maria Sebastian, Rosa
    Vallribera, Adelina
    Francisco Civicos, Jose
    Najera, Carmen
    TETRAHEDRON, 2013, 69 (12) : 2655 - 2659
  • [3] HECK-MATSUDA REACTION UTILIZING IN-SITU GENERATED PALLADIUM ON ALUMINUM PHOSPHATE
    Stern, Therese
    Heyde , Sandra
    Brunner, Heiko
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2022, 36 (02) : 423 - 432
  • [4] Continuous-Flow Heck-Matsuda Reaction: Homogeneous versus Heterogeneous Palladium Catalysts
    Oger, Nicolas
    Le Grognec, Erwan
    Felpin, Francois-Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8255 - 8262
  • [5] Recent advances in the Heck-Matsuda reaction in heterocyclic chemistry
    Felpin, Francois-Xavier
    Nassar-Hardy, Luma
    Le Callonnec, Francois
    Fouquet, Eric
    TETRAHEDRON, 2011, 67 (16) : 2815 - 2831
  • [6] Highly diastereoselective Heck-Matsuda reaction with pyrazolyl diazonium salts
    Bertozzi, F.
    Bertozzi, F.
    Bertozzi, S. M.
    Bandiera, T.
    Bertozzi, F.
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (21) : 9994 - 9997
  • [7] Heck-Matsuda Reactions Catalyzed by a Hydroxyalkyl-Functionalized NHC and Palladium Acetate
    Penafiel, Itziar
    Pastor, Isidro M.
    Yus, Miguel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (16) : 3151 - 3156
  • [8] Steric evaluation of Pyox ligands for asymmetric intermolecular Heck-Matsuda reaction
    Bibi, Rifhat
    Khan, Ismat Ullah
    Hassan, Abbas
    TETRAHEDRON LETTERS, 2022, 111
  • [9] General strategy for sphingosine congeners synthesis via Heck-Matsuda reaction
    Grigol Martinez, Pablo David
    Duarte Correia, Carlos Roque
    Dal Poggetto, Guilherme Fonseca
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [10] Palladium-Catalyzed Asymmetric Heck-Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts
    Jiang, Ze-Zhen
    Jiang, Yang-Jie
    Du, Juan
    Chen, Di
    Ding, Chang-Hua
    Xu, Bin
    Hou, Xue-Long
    SYNTHESIS-STUTTGART, 2019, 51 (17): : 3269 - 3276