Suzuki-Miyaura reactions of arenediazonium salts catalyzed by Pd(0)/C. One-pot chemoselective double cross-coupling reactions

被引：99
|
作者：
Taylor, Rachel H. [1 ]
Felpin, Francois-Xavier [1 ]
机构：
[1] Univ Bordeaux 1, CNRS, Inst Sci Mol, F-33405 Talence, France
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 15期
关键词：
D O I：
10.1021/ol0712733
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Suzuki-Miyaura cross-coupling of arenediazonium tetrafluoroborate salts with boronic acid partners catalyzed by Pd(0)/C is described as a practical and efficient alternative to classical homogeneous conditions. Reactions conducted in alcoholic solvents proved to be extremely fast using mild conditions. Additionnaly, we developed a chemoselective double Suzuki-Miyaura cross-coupling in a single reaction vessel allowing the synthesis of unsymmetrical terphenyls.
引用
收藏
页码：2911 / 2914
页数：4
相关论文
共 50 条
  • [1] Pd/C-catalyzed one-pot Suzuki-Miyaura cross-coupling/hydrogenation of pyridine derivatives
    Pitna, Dinda B.
    Tanaka, Nao
    Usuki, Toyonobu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2021, 58 (10) : 2039 - 2044
  • [2] One-pot synthesis of chromenes by Suzuki-Miyaura cross-coupling reactions with benzyl bromides
    Ahmed, Atiur
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2019, 96 (11) : 1429 - 1432
  • [3] Impact of Solvent and Their Contaminants on Pd/C Catalyzed Suzuki-Miyaura Cross-Coupling Reactions
    de Lambert de Boisjan, Alexandre
    Allemann, Christophe
    Fadini, Luca
    HELVETICA CHIMICA ACTA, 2021, 104 (06)
  • [4] 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
  • [5] Nanoparticles Pd-Catalyzed Suzuki and Heck Cross-Coupling Reactions of Arenediazonium Tetrafluoroborate Salts
    Zhao, Xiaoxia
    Chang, Honghong
    Li, Xing
    Wei, Wenlong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (02) : 478 - 483
  • [6] Facile and economical Miyaura borylation and one-pot Suzuki-Miyaura cross-coupling reaction
    Boontiem, Phongsakorn
    Kiatisevi, Supavadee
    INORGANICA CHIMICA ACTA, 2020, 506
  • [7] Efficient One-Pot Suzuki-Miyaura Double Cross-Coupling Reactions Using Very Low Pd(PPh3)4 Catalyst Loading
    Habashneh, Almeqdad Y.
    Dakhil, Othman O.
    Zein, Ahmed
    Georghiou, Paris E.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (23) : 4221 - 4229
  • [8] One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki-Miyaura Cross-Coupling
    Baumgartner, Yann
    Baudoin, Olivier
    ACS CATALYSIS, 2020, 10 (18) : 10508 - 10515
  • [9] Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts
    Schmidt, Bernd
    Hoelter, Frank
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) : 4914 - 4920
  • [10] Recent Advances in Pd-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions with Triflates or Nonaflates
    Degli Innocenti, Maria
    Schreiner, Till
    Breinbauer, Rolf
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4086 - 4120
12345