Synthesis of 2,2′-Bipyridines via Suzuki-Miyaura Cross-Coupling

被引:28
|
作者
Guetz, Christoph [1 ]
Luetzen, Arne [1 ]
机构
[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
来源
SYNTHESIS-STUTTGART | 2010年 / 01期
关键词
cross-coupling reactions; bipyridines; palladium; 2-pyridylboronic acid esters; Suzuki-Miyaura reaction; BIPYRIDINE; PYRIDINES; ESTERS; ACIDS;
D O I
10.1055/s-0029-1217082
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
For a long time, the Suzuki-Miyaura cross-coupling reaction could not be used for the synthesis of 2,2'-bipyridines due to the lack of sufficiently stable 2-pyridylboron compounds. Stabilized 2-pyridylboronic acid esters recently developed by Hodgson, however, were found to be ideally suited for this purpose. Two general protocols could be developed and demonstrated to be valuable alternatives, which can be used very efficiently for the synthesis of functionalized 2,2'-bipyridines.
引用
收藏
页码:85 / 90
页数:6
相关论文
共 50 条
  • [21] Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki-Miyaura Cross-Coupling Reactions
    Fang, Yewen
    Zhang, Li
    Li, Jinjian
    Jin, Xiaoping
    Yuan, Meijuan
    Li, Ruifeng
    Wu, Rong
    Fang, Jianghua
    ORGANIC LETTERS, 2015, 17 (04) : 798 - 801
  • [22] Expedient synthesis of 4-O-methylhonokiol via Suzuki-Miyaura cross-coupling
    Kwak, Jae-Hwan
    Cho, Young Ae
    Jang, Jae-Yong
    Seo, Seung-Yong
    Lee, Heesoon
    Hong, Jin Tae
    Han, Sang-Bae
    Lee, Kiho
    Kwak, Young-Shin
    Jung, Jae-Kyung
    TETRAHEDRON, 2011, 67 (48) : 9401 - 9404
  • [23] Mechanochemical Synthesis of Ketones via Chemoselective Suzuki-Miyaura Cross-Coupling of Acyl Chlorides
    Zhang, Jin
    Zhang, Pei
    Ma, Yangmin
    Szostak, Michal
    ORGANIC LETTERS, 2022, 24 (12) : 2338 - 2343
  • [24] Site Selective Synthesis of Pentaarylpyridines via Multiple Suzuki-Miyaura Cross-Coupling Reactions
    Reimann, Sebastian
    Ehlers, Peter
    Petrosyan, Andranik
    Kohse, Stefanie
    Spannenberg, Anke
    Surkus, Annette E.
    Ghochikyan, Tariel V.
    Saghyan, Ashot S.
    Lochbrunner, Stefan
    Kuehn, Oliver
    Ludwig, Ralf
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 1987 - 2008
  • [25] An approach to heterodiarylmethanes via sp2-sp3 Suzuki-Miyaura cross-coupling
    Stewart, Gavin W.
    Maligres, Peter E.
    Baxter, Carl A.
    Junker, Ellyn M.
    Krska, Shane W.
    Scott, Jeremy P.
    TETRAHEDRON, 2016, 72 (26) : 3701 - 3706
  • [26] Postsynthetic Modification of Peptoids via the Suzuki-Miyaura Cross-Coupling Reaction
    Nam, Ho Yeon
    Seo, Jiwon
    BIOPOLYMERS, 2016, 106 (01) : 82 - 88
  • [27] Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki-Miyaura cross-coupling
    Reyes, Samuel
    Huigens, Robert W., III
    Su, Zhaoming
    Simon, Michel L.
    Melander, Christian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 3041 - 3049
  • [28] Azidosubstituted arylboronic acids: synthesis and Suzuki-Miyaura cross-coupling reactions
    Sviridov, SI
    Vasi'ev, AA
    Sergovskaya, NL
    Chirskaya, MV
    Shorshnev, SV
    TETRAHEDRON, 2006, 62 (11) : 2639 - 2647
  • [29] Chemoselective Synthesis of Arylpyridines through Suzuki-Miyaura Cross-Coupling Reactions
    Perdomo Rivera, Rodisnel
    Ehlers, Peter
    Ohlendorf, Lars
    Torres Rodriguez, Eugenio
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (08) : 990 - 1003
  • [30] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
    Kotha, S
    Lahiri, K
    Kashinath, D
    TETRAHEDRON, 2002, 58 (48) : 9633 - 9695