Suzuki-Miyaura Coupling Using Monolithic Pd Reactors and Scaling-Up by Series Connection of the Reactors

被引:20
|
作者
Nagaki, Aiichiro [1 ]
Hirose, Katsuyuki [1 ]
Moriwaki, Yuya [1 ]
Takumi, Masahiro [1 ]
Takahashi, Yusuke [1 ]
Mitamura, Koji [2 ]
Matsukawa, Kimihiro [2 ]
Ishizuka, Norio [3 ]
Yoshida, Jun-ichi [4 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Nishikyo Ku, Kyoto 6158510, Japan
[2] Osaka Municipal Tech Res Inst, Elect Mat Res Div, Joto Ku, 1-6-50 Morinomiya, Osaka 5368553, Japan
[3] Emaus Kyoto Inc, R&D, Ukyo Ku, 26 Nishida Cho, Kyoto 6150055, Japan
[4] Natl Inst Technol, Suzuka Coll, Shiroko Cho, Suzuka, Mie 5100294, Japan
来源
CATALYSTS | 2019年 / 9卷 / 03期
基金
日本科学技术振兴机构;
关键词
flow synthesis; monolith reactors; CONTINUOUS-FLOW SYNTHESIS; PALLADIUM-CATALYZED BORYLATION; FLASH CHEMISTRY; SPACE INTEGRATION; ORGANIC-SYNTHESIS; ARYLBORONIC ESTERS; ARYL CHLORIDES; BOND FORMATION; EFFICIENT; MICROREACTORS;
D O I
10.3390/catal9030300
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The space integration of the lithiation of aryl halides, the borylation of aryllithiums, and Suzuki-Miyaura coupling using a Pd catalyst supported by a polymer monolith flow reactor without using an intentionally added base was achieved. To scale up the process, a series connection of the monolith Pd reactor was examined. To suppress the increase in the pressure drop caused by the series connection, a monolith reactor having larger pore sizes was developed by varying the temperature of the monolith preparation. The monolithic Pd reactor having larger pore sizes enabled Suzuki-Miyaura coupling at a higher flow rate because of a lower pressure drop and, therefore, an increase in productivity. The present study indicates that series connection of the reactors with a higher flow rate serves as a good method for increasing the productivity without decreasing the yields.
引用
收藏
页数:24
相关论文
共 50 条
  • [41] Total Synthesis of (-)-Batrachotoxin Enabled by a Pd/Ag-Promoted Suzuki-Miyaura Coupling Reaction
    Watanabe, Yuuki
    Morozumi, Hisahiro
    Mutoh, Hiroyuki
    Hagiwara, Koichi
    Inoue, Masayuki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023,
  • [42] Pd@UiO-66: An Efficient Catalyst for Suzuki-Miyaura Coupling Reaction at Mild Condition
    Dong, Wenhuan
    Feng, Cheng
    Zhang, Li
    Shang, Ningzhao
    Gao, Shutao
    Wang, Chun
    Wang, Zhi
    CATALYSIS LETTERS, 2016, 146 (01) : 117 - 125
  • [43] Photoaccelerated Suzuki-Miyaura and Sonogashira coupling reactions catalyzed by an Ir-Pd binuclear complex
    Yang, Chung-Hao
    Liu, Yi-Hung
    Peng, Shie-Ming
    Liu, Shiuh-Tzung
    MOLECULAR CATALYSIS, 2022, 522
  • [44] Total Synthesis of (-)-Batrachotoxin Enabled by a Pd/Ag-Promoted Suzuki-Miyaura Coupling Reaction
    Watanabe, Yuuki
    Morozumi, Hisahiro
    Mutoh, Hiroyuki
    Hagiwara, Koichi
    Inoue, Masayuki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [45] Pd/REOs catalysts applied to the Suzuki-Miyaura coupling. A comparison of their catalytic performance and reusability
    Del Zotto, Alessandro
    Colussi, Sara
    Trovarelli, Alessandro
    INORGANICA CHIMICA ACTA, 2018, 470 : 275 - 283
  • [46] A highly effective azetidine-Pd(II) catalyst for Suzuki-Miyaura coupling reactions in water
    Lee, Dong-Hwan
    Lee, Young Hoon
    Kim, Dong Il
    Kim, Yang
    Lim, Woo Taik
    Harrowfield, Jack M.
    Thuery, Pierre
    Jin, Myung-Jong
    Park, Yu Chul
    Lee, Ik-Mo
    TETRAHEDRON, 2008, 64 (30-31) : 7178 - 7182
  • [47] 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
  • [48] 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
  • [49] Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides
    Lei, Peng
    Meng, Guangrong
    Ling, Yun
    An, Jie
    Szostak, Michal
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13): : 6638 - 6646
  • [50] 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