Chan-Lam-Type C-N Cross-Coupling Reactions under Base-and Ligand-Free CuI-Zeolite Catalysis

被引：24
作者：
Garnier, Tony [1 ]
Sakly, Randa [1 ,2 ]
Danel, Mathieu [1 ]
Chassaing, Stefan [1 ]
Pale, Patrick [3 ]
机构：
[1] Univ Toulouse, Inst Technol Avancees Sci Vivant ITAV, CNRS, UPS, 1 Pl Pierre Potier, F-31106 Toulouse 1, France
[2] Univ Monastir, Fac Sci Monastir, LCOHPNR, Monastir, Tunisia
[3] Univ Strasbourg, CNRS, Lab Synthese React Organ & Catalyse LASYROC, Inst Chim,UMR7177, 4 Rue Blaise Pascal, F-67070 Strasbourg, France
来源：
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 06期
关键词：
copper; zeolites; heterogeneous catalysis; cross-coupling; Chan-Lam reaction; C-N bond formation; ARYLBORONIC ACIDS; CLICK CHEMISTRY; COPPER; ARYLATION; PHENYL; AMINES;
D O I：
10.1055/s-0036-1588652
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan-Lam cross-coupling reactions. Cu-I-USY appeared as the best catalyst and proved to efficiently promote C-N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base.
引用
收藏
页码：1223 / 1230
页数：8
相关论文
共 52 条
  • [1] 'Click chemistry' in CuI-zeolites:: a convenient access to glycoconjugates
    Alix, Aurlien
    Chassaing, Stefan
    Pale, Patrick
    Sommer, Jean
    [J]. TETRAHEDRON, 2008, 64 (37) : 8922 - 8929
  • [2] Mechanism of Palladium-Catalyzed Suzuki-Miyaura Reactions: Multiple and Antagonistic Roles of Anionic "Bases" and Their Countercations
    Amatore, Christian
    Le Duc, Gaetan
    Jutand, Anny
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (31) : 10082 - 10093
  • [3] Ann W., 1957, ANN CHIM, V2, P819
  • [4] Natural Indian Natrolite zeolite-supported Cu nanoparticles: a new and reusable heterogeneous catalyst for N-arylation of sulfonamides with boronic acids in water under ligand-free conditions
    Azarifar, Davood
    Soleimanei, Fatemeh
    [J]. RSC ADVANCES, 2014, 4 (24): : 12119 - 12126
  • [5] Barboro P., 2010, HETEROGENIZED HOMOGE
  • [6] Copper in cross-coupling reactions - The post-Ullmann chemistry
    Beletskaya, IP
    Cheprakov, AV
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
  • [7] Zeo-click synthesis: CuI-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds
    Beneteau, Valerie
    Olmos, Andrea
    Boningari, Thirupathi
    Sommer, Jean
    Pale, Patrick
    [J]. TETRAHEDRON LETTERS, 2010, 51 (28) : 3673 - 3677
  • [8] Boringari T., 2010, EUR J ORG CHEM, P6338
  • [9] Direct observation of CuI/CuIII redox steps relevant to Ullmann-type coupling reactions
    Casitas, Alicia
    King, Amanda E.
    Parella, Teodor
    Costas, Miquel
    Stahl, Shannon S.
    Ribas, Xavi
    [J]. CHEMICAL SCIENCE, 2010, 1 (03) : 326 - 330
  • [10] Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates
    Chan, DMT
    Monaco, KL
    Li, RH
    Bonne, D
    Clark, CG
    Lam, PYS
    [J]. TETRAHEDRON LETTERS, 2003, 44 (19) : 3863 - 3865
123456