A new green catalytic method for biaryl cross-coupling and oligothiophene synthesis

被引:12
|
作者
Sévignon, M [1 ]
Hassan, J [1 ]
Gozzi, C [1 ]
Schulz, E [1 ]
Lemaire, M [1 ]
机构
[1] Univ Lyon 1, CPE Lyon, Lab Catalyse & Synth Organ, UMR 5622, F-69622 Villeurbanne, France
关键词
Heck reaction; aryl-aryl cross-coupling; thiophene derivatives; oligomerization;
D O I
10.1016/S1387-1609(00)00151-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct aryltion of activated thiophenes is achieved in moderate to good yields using a Heck-type reaction with a mixture of Pd(OAc)(2), n-Bu4NBr and a base as catalytic system. This new procedure is applied to different 2- and 3-substituted thiophenes, and parameters of thr reaction are studied. Based on these results, 3 new method for polymerization of various 2 -halogeno-3-alkylthiophenes is described using the same catalytic system and leading to expected regioregular functionalized oligomers with good yields.
引用
收藏
页码:569 / 572
页数:4
相关论文
共 50 条
  • [41] Green Suzuki-Miyaura cross-coupling for the synthesis of chiral biaryls
    Dotsenko, Irina A.
    Shishkina, Irina N.
    Demyanovich, Valeria M.
    Bumagin, Nikolay A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [42] Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling
    Herrbach, A
    Marinetti, A
    Baudoin, O
    Guénard, D
    Guéritte, F
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12): : 4897 - 4905
  • [43] Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates
    Molander, Gary A.
    Fleury-Bregeot, Nicolas
    Hiebel, Marie-Aude
    ORGANIC LETTERS, 2011, 13 (07) : 1694 - 1697
  • [44] Asymmetric Suzuki-Miyaura Cross-Coupling for the Synthesis of Chiral Biaryl Compounds as Potential Monophosphine Ligands
    Ma, Yan-Na
    Yang, Shang-Dong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (18) : 6673 - 6677
  • [45] Effective biaryl compound synthesis using cross-coupling reaction with nickel complexes coordinated by diaminophosphine ligands
    Yamada, I
    Yamazaki, N
    Yamaguchi, M
    Yamagishi, T
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 120 (1-3) : L13 - L15
  • [46] Direct catalytic cross-coupling of organolithium compounds
    Giannerini M.
    Fañanás-Mastral M.
    Feringa B.L.
    Nature Chemistry, 2013, 5 (8) : 667 - 672
  • [47] Direct catalytic cross-coupling of organolithium compounds
    Hornillos, Valentin
    Giannerini, Massimo
    Vila, Carlos
    Fananas-Mastral, Martin
    Feringa, Ben L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [48] Direct catalytic cross-coupling of organolithium compounds
    Giannerini, Massimo
    Fananas-Mastral, Martin
    Feringa, Ben L.
    NATURE CHEMISTRY, 2013, 5 (08) : 667 - 672
  • [49] Catalytic Asymmetric Imine Cross-Coupling Reaction
    Han, Xiang-Lei
    Hu, Bin
    Fei, Chao
    Li, Zhe
    Yu, Yang
    Cheng, Cheng
    Foxman, Bruce
    Luo, Jisheng
    Deng, Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (08) : 4400 - 4407
  • [50] Direct catalytic cross-coupling of alkenyllithium compounds
    Hornillos, Valentin
    Giannerini, Massimo
    Vila, Carlos
    Fananas-Mastral, Martin
    Feringa, Ben L.
    CHEMICAL SCIENCE, 2015, 6 (02) : 1394 - 1398