Simple pyridylmethylamines: efficient and robust N,N-ligands for Suzuki-Miyaura coupling reactions

被引:12
作者
Gunawan, Maria-Agatha [2 ,3 ]
Qiao, Chunjing [2 ,3 ]
Abrunhosa-Thomas, Isabelle [2 ,3 ]
Puget, Bertrand [2 ,3 ]
Roblin, Jean-Philippe [2 ,3 ]
Prim, Damien [1 ]
Troin, Yves [2 ,3 ]
机构
[1] Univ Versailles St Quentin, ILV, UMR CNRS 8180, F-78035 Versailles, France
[2] Clermont Univ, ENSCCF, EA 987, LCHG, F-63000 Clermont Ferrand, France
[3] Ensemble Sci Cezeaux, F-63174 Aubiere, France
关键词
Pyridylmethyla mines; N; N-Ligands; Suzuki-Miyaura; LIGAND-FREE; HETEROGENEOUS PALLADIUM; RECYCLABLE CATALYSTS; COMPLEXES; NANOPARTICLES;
D O I
10.1016/j.tetlet.2010.07.151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of pyridylmethylamines have been synthesized in one step from commercially available starting material and identified as effective ligands for Pd-catalyzed carbon-carbon bond formation through Suzuki-Miyaura coupling reaction. The N,N-pyridylmethylamine-Pd catalytic systems appeared as an interesting and robust compromise between catalytic efficiency, substrate compatibility, and practical aspects. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5392 / 5394
页数:3
相关论文
共 28 条
  • [1] PEG350-based di-(2-pyridyl)methylamine as a ligand in the Pd-catalyzed water Suzuki-Miyaura reaction of aryl chlorides
    Adidou, Oluissam
    Goux-Henry, Catherine
    Safi, Mohamed
    Soufiaoui, Mohamed
    Framery, Eric
    [J]. TETRAHEDRON LETTERS, 2008, 49 (50) : 7217 - 7219
  • [2] Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media
    Alacid, Emilio
    Najera, Carmen
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (11) : 1658 - 1665
  • [3] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view
    Astruc, Didier
    [J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1884 - 1894
  • [4] The 1,3-Diaminobenzene-Derived Aminophosphine Palladium Pincer Complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A Highly Active Suzuki-Miyaura Catalyst with Excellent Functional Group Tolerance
    Bolliger, Jeanne L.
    Frech, Christian M.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 1075 - 1080
  • [5] CAL V, 2009, J ORG CHEM, V70, P6040
  • [6] [Pd(HQS)2] (HQS=8-hydroxyquinoline-5-sulfonic acid) a highly efficient catalyst for Suzuki-Miyaura cross couplings in water
    Conelly-Espinosa, Patricia
    Morales-Morales, David
    [J]. INORGANICA CHIMICA ACTA, 2010, 363 (06) : 1311 - 1315
  • [7] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710
  • [8] Heterogeneous Suzuki and Stille coupling reactions using highly efficient palladium(0) immobilized MCM-41 catalyst
    Jana, Sreyashi
    Haidar, Satyajit
    Koner, Subratanath
    [J]. TETRAHEDRON LETTERS, 2009, 50 (34) : 4820 - 4823
  • [9] Heterogeneous Pd/C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters
    Kitamura, Yoshiaki
    Sakurai, Ai
    Udzu, Takahiro
    Maegawa, Tomohiro
    Monguchi, Yasunari
    Sajiki, Hironao
    [J]. TETRAHEDRON, 2007, 63 (43) : 10596 - 10602
  • [10] Ligand-Free and Heterogeneous Palladium on Carbon-Catalyzed Hetero-Suzuki-Miyaura Cross-Coupling
    Kitamura, Yoshiaki
    Sako, Satoko
    Tsutsui, Azusa
    Monguchi, Yasunari
    Maegawa, Tomohiro
    Kitade, Yukio
    Sajiki, Hironao
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) : 718 - 730