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 [J].
Adidou, Oluissam ;
Goux-Henry, Catherine ;
Safi, Mohamed ;
Soufiaoui, Mohamed ;
Framery, Eric .
TETRAHEDRON LETTERS, 2008, 49 (50) :7217-7219
[2]   Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki-Miyaura reactions in aqueous media [J].
Alacid, Emilio ;
Najera, Carmen .
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 [J].
Astruc, Didier .
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 [J].
Bolliger, Jeanne L. ;
Frech, Christian M. .
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 [J].
Conelly-Espinosa, Patricia ;
Morales-Morales, David .
INORGANICA CHIMICA ACTA, 2010, 363 (06) :1311-1315
[7]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710
[8]   Heterogeneous Suzuki and Stille coupling reactions using highly efficient palladium(0) immobilized MCM-41 catalyst [J].
Jana, Sreyashi ;
Haidar, Satyajit ;
Koner, Subratanath .
TETRAHEDRON LETTERS, 2009, 50 (34) :4820-4823
[9]   Heterogeneous Pd/C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters [J].
Kitamura, Yoshiaki ;
Sakurai, Ai ;
Udzu, Takahiro ;
Maegawa, Tomohiro ;
Monguchi, Yasunari ;
Sajiki, Hironao .
TETRAHEDRON, 2007, 63 (43) :10596-10602
[10]   Ligand-Free and Heterogeneous Palladium on Carbon-Catalyzed Hetero-Suzuki-Miyaura Cross-Coupling [J].
Kitamura, Yoshiaki ;
Sako, Satoko ;
Tsutsui, Azusa ;
Monguchi, Yasunari ;
Maegawa, Tomohiro ;
Kitade, Yukio ;
Sajiki, Hironao .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) :718-730