Palladium-catalyzed decarbonylative and decarboxylative cross-coupling of acyl chlorides with potassium perfluorobenzoates affording unsymmetrical biaryls

被引:9
|
作者
Fu, Liyan [1 ]
You, Jingwen [1 ]
Nishihara, Yasushi [2 ]
机构
[1] Okayama Univ, Grad Sch Nat Sci & Technol, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan
[2] Okayama Univ, Res Inst Interdisciplinary Sci, Kita Ku, 3-1-1 Tsushimanaka, Okayama 7008530, Japan
关键词
Chlorine compounds;
D O I
10.1039/d1cc00202c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper describes the synthesis of unsymmetrical biaryls by the palladium-catalyzed cross-coupling reaction of acyl chlorides with potassium perfluorobenzoates. This transformation is unique in that it involves simultaneous decarbonylation and decarboxylation under redox-neutral conditions. Compared to conventional cross-coupling protocols for the synthesis of unsymmetrical biaryls, the two reactants in this synthetic strategy can be readily prepared from abundant and inexpensive aromatic carboxylic acids.
引用
收藏
页码:3696 / 3699
页数:4
相关论文
共 50 条
  • [1] Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates
    Fu, Liyan
    Chen, Qiang
    Nishihara, Yasushi
    ORGANIC LETTERS, 2020, 22 (16) : 6388 - 6393
  • [2] Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes
    Lerebours, R
    Camacho-Soto, A
    Wolf, C
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21): : 8601 - 8604
  • [3] Palladium-Catalyzed Cross-Coupling of Tertiary Cyclopropyl Carbagermatranes with Acyl Chlorides
    Yang, Shuo
    Chen, Guang
    Xu, Qing-Hao
    Xiao, Bin
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (12)
  • [4] Additive-Free Palladium-Catalyzed Decarboxylative Cross-Coupling of Aryl Chlorides
    Daley, Ryan A.
    Liu, En-Chih
    Topczewski, Joseph J.
    ORGANIC LETTERS, 2019, 21 (12) : 4734 - 4738
  • [5] Palladium-catalyzed Decarbonylative Cyanation of Acyl Fluorides and Chlorides
    Sakurai, Shun
    Tobisu, Mamoru
    CHEMISTRY LETTERS, 2021, 50 (01) : 151 - 153
  • [6] Palladium/copper-catalyzed decarboxylative cross-coupling of aryl chlorides with potassium carboxylates
    Goossen, Lukas J.
    Zimmermann, Bettina
    Knauber, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (37) : 7103 - 7106
  • [7] Synthesis of Biaryls via Decarbonylative Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Carboxylic Acids
    Liu, Chengwei
    Ji, Chong-Lei
    Qin, Zhi-Xin
    Hong, Xin
    Szostak, Michal
    ISCIENCE, 2019, 19 : 749 - +
  • [8] Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids
    Muto, Kei
    Hatakeyama, Taito
    Itami, Kenichiro
    Yamaguchi, Junichiro
    ORGANIC LETTERS, 2016, 18 (19) : 5106 - 5109
  • [9] SELECTIVE SYNTHESIS OF UNSYMMETRICAL BIARYLS VIA PALLADIUM-CATALYZED CROSS-COUPLING OF ARYLFLUOROSILANES WITH ARYL IODIDES
    HATANAKA, Y
    FUKUSHIMA, S
    HIYAMA, T
    CHEMISTRY LETTERS, 1989, (10) : 1711 - 1714
  • [10] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL CHLORIDES WITH ARYLSILATRANES
    Yamamoto, Yutaro
    Baralle, Alexandre
    Godefroy, Anais
    Murakami, Kei
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    HETEROCYCLES, 2017, 95 (01) : 568 - 574