Classical Reagents: New Surprises in Palladium-Catalyzed C-C Coupling Reactions

被引：30
作者：
Lindhardt, Anders T. [1 ,2 ]
Skrydstrup, Troels [1 ,2 ]
机构：
[1] Aarhus Univ, Dept Chem, Ctr Insoluble Prot Struct inSPIN, DK-8000 Aarhus, Denmark
[2] Aarhus Univ, Interdisciplinary Nanosci Ctr, DK-8000 Aarhus, Denmark
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 29期
基金：
新加坡国家研究基金会;
关键词：
alkynes; hydride elimination; C-C coupling reactions; hydropalladation; palladium;
D O I：
10.1002/chem.200800608
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
From investigations on a relatively simple concept to identify conditions for promoting Mizoroki-Heck reactions with vinyl tosylates and phosphates, two serendipitous discoveries were made concerning new properties of palladium as a catalyst. In the first case, beta-hydride eliminations well known for alkyl metal complexes were found to be equally feasible with alkenyl metal compounds. And secondly, conditions were found for promoting intermolecular ene-yne couplings via a Pd-II-H intermediate. This coupling reactions represents an atom economical Mizoroki-Heck type reaction.
引用
收藏
页码：8756 / 8766
页数：11
相关论文
共 76 条
  • [1] Palladium(0) alkyne complexes as active species: a DFT investigation
    Ahlquist, M
    Fabrizi, G
    Cacchi, S
    Norrby, PO
    [J]. CHEMICAL COMMUNICATIONS, 2005, (33) : 4196 - 4198
  • [2] The mechanism of the phosphine-free palladium-catalyzed hydroarylation of alkynes
    Ahlquist, Marten
    Fabrizi, Giancarlo
    Cacchi, Sandro
    Norrby, Per-Ola
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12785 - 12793
  • [3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [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] Rate and mechanism of the heck reactions of arylpalladium complexes ligated by a bidentate P,P ligand with an electron-rich alkene (isobutyl vinyl ether)
    Amatore, Christian
    Godin, Beatrice
    Jutand, Anny
    Lemaitre, Frederic
    [J]. ORGANOMETALLICS, 2007, 26 (07) : 1757 - 1761
  • [6] Rate and mechanism of the reaction of alkenes with aryl palladium complexes ligated by a bidentate PP ligand in Heck reactions
    Amatore, Christian
    Godin, Beatrice
    Jutand, Anny
    Lemaitre, Frederic
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (07) : 2002 - 2011
  • [7] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [8] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
    Billingsley, Kelvin
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3358 - 3366
  • [9] BUCHWALD, 2005, CHEM COMMUN, P431
  • [10] Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
12345678