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
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
  • [31] Synthesis of Biaryls through a One-Pot Tandem Borylation/Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by a Palladacycle
    Wang, Lianhui
    Cui, Xiuling
    Li, Jingya
    Wu, Yusheng
    Zhu, Zhiwu
    Wu, Yangjie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (03) : 595 - 603
  • [32] Pd catalysts supported on hydrogen titanate nanotubes for Suzuki-Miyaura cross-coupling reactions
    Martinez-Klimov, Mark E.
    Hernandez-Hipolito, Patricia
    Martinez-Garcia, Marcos
    Klimova, Tatiana E.
    CATALYSIS TODAY, 2018, 305 : 58 - 64
  • [33] Magnetic Pd-Fe nanoparticles for sustainable Suzuki-Miyaura cross-coupling reactions
    Zhu, Zhuangli
    Liang, Sanqi
    Sun, Huaming
    Zhang, Weiqiang
    Yang, Jianming
    Gao, Ziwei
    CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (11) : 3176 - 3183
  • [34] Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction
    Chen, You
    Peng, Hui
    Pi, Yun-Xiao
    Meng, Tong
    Lian, Ze-Yu
    Yan, Meng-Qi
    Liu, Yan
    Liu, Sheng-Hua
    Yu, Guang-Ao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) : 3236 - 3242
  • [35] Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions
    Mojtaba Amini
    Mojtaba Bagherzadeh
    Sadegh Rostamnia
    ChineseChemicalLetters, 2013, 24 (05) : 433 - 436
  • [36] Controllable deposition of dispersed Pd nanoparticles on ZnO for Suzuki-Miyaura cross-coupling reactions
    Bressi, Viviana
    Len, Thomas
    Polidoro, Daniele
    Esposito, Roberto
    Mazur, Michal
    Selva, Maurizio
    Espro, Claudia
    Luque, Rafael
    DALTON TRANSACTIONS, 2023, 52 (46) : 17279 - 17288
  • [37] Base-free Pd-MOF catalyzed the Suzuki-Miyaura cross-coupling reaction of arenediazonium tetrafluoroborate salts with arylboronic acids
    Liu, Yangyang
    Wang, Jie
    Li, Tang
    Zhao, Zesheng
    Pang, Wan
    TETRAHEDRON, 2019, 75 (40)
  • [38] Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions
    Amini, Mojtaba
    Bagherzadeh, Mojtaba
    Rostamnia, Sadegh
    CHINESE CHEMICAL LETTERS, 2013, 24 (05) : 433 - 436
  • [39] Progress of Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions of Phenol Derivatives
    Chen, Guojun
    Du, Jianshi
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (01) : 65 - 80
  • [40] Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters
    Buchspies, Jonathan
    Pyle, Daniel J.
    He, Huixin
    Szostak, Michal
    MOLECULES, 2018, 23 (12):