"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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 20期
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
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共 57 条
  • [1] Observation of Binuclear Palladium Clusters upon ESI-MS Monitoring of the Suzuki-Miyaura Cross-Coupling Catalyzed by a Dichloro-bis(aminophosphine) Complex of Palladium
    Agrawal, Divya
    Schroeder, Detlef
    Frech, Christian M.
    [J]. ORGANOMETALLICS, 2011, 30 (13) : 3579 - 3587
  • [2] Insight into Solution Chemistry from Gas-Phase Experiments
    Agrawal, Divya
    Schroeder, Detlef
    [J]. ORGANOMETALLICS, 2011, 30 (01) : 32 - 35
  • [3] Ambient mass spectrometry: bringing MS into the "real world"
    Alberici, Rosana M.
    Simas, Rosineide C.
    Sanvido, Gustavo B.
    Romao, Wanderson
    Lalli, Priscila M.
    Benassi, Mario
    Cunha, Ildenize B. S.
    Eberlin, Marcos N.
    [J]. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2010, 398 (01) : 265 - 294
  • [4] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction
    Alonso, F
    Beletskaya, IP
    Yus, M
    [J]. TETRAHEDRON, 2005, 61 (50) : 11771 - 11835
  • [5] Mechanism and synthesis of pharmacologically active quinolones from Morita-Baylis-Hillman adducts
    Amarante, Giovanni W.
    Benassi, Mario
    Pascoal, Robert N.
    Eberlin, Marcos N.
    Coelho, Fernando
    [J]. TETRAHEDRON, 2010, 66 (24) : 4370 - 4376
  • [6] Bronsted Acid Catalyzed Morita-Baylis-Hillman Reaction: A New Mechanistic View for Thioureas Revealed by ESI-MS(/MS) Monitoring and DFT Calculations
    Amarante, Giovanni W.
    Benassi, Mario
    Milagre, Humberto M. S.
    Braga, Ataualpa A. C.
    Maseras, Feliu
    Eberlin, Marcos N.
    Coelho, Fernando
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (45) : 12460 - 12469
  • [7] Dualistic Nature of the Mechanism of the Morita-Baylis-Hillman Reaction Probed by Electrospray Ionization Mass Spectrometry
    Amarante, Giovanni W.
    Milagre, Humberto M. S.
    Vaz, Boniek G.
    Ferreira, Bruno R. Vilacha
    Eberlin, Marcos N.
    Coelho, Fernando
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) : 3031 - 3037
  • [8] Unusual selectivity-determining factors in the phosphine-free Heck arylation of allyl ethers
    Ambrogio, Ilaria
    Fabrizi, Giancarlo
    Cacchi, Sandro
    Henriksen, Signe Teuber
    Fristrup, Peter
    Tanner, David
    Norrby, Per-Ola
    [J]. ORGANOMETALLICS, 2008, 27 (13) : 3187 - 3195
  • [9] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions
    Arpad Molnar
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 2251 - 2320
  • [10] Microwave-Assisted Palladium(II)-Catalyzed Synthesis of Aryl Ketones from Aryl Sulfinates and Direct ESI-MS Studies Thereof
    Behrends, Malte
    Savmarker, Jonas
    Sjoberg, Per J. R.
    Larhed, Mats
    [J]. ACS CATALYSIS, 2011, 1 (11): : 1455 - 1459
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