Ether-lmidazolium Carbenes for Suzuki-Miyaura Cross-Coupling of Heteroaryl Chlorides with Aryl/Heteroarylboron Reagents

被引:38
|
作者
Kuriyama, Masami [1 ]
Matsuo, Seira [1 ]
Shinozawa, Mina [1 ]
Onomura, Osamu [1 ]
机构
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
关键词
ORTHO-SUBSTITUTED BIARYLS; ARYL CHLORIDES; PALLADIUM PRECATALYST; GENERAL-METHOD; BORONIC ACIDS; COMPLEXES; CATALYSTS; LIGANDS; NHC; ROBUST;
D O I
10.1021/ol4010189
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Easily accessible and handled ether-imidazolium chlorides were developed as ligand precursors. The coupling reactions of heteroaryl chlorides with aryl/heteroarylboronic acids and esters were catalyzed by the palladium/ether-imidazolium chloride system with high substrate tolerance to give various heterobiaryls in good to excellent yields.
引用
收藏
页码:2716 / 2719
页数:4
相关论文
共 50 条
  • [1] Suzuki-Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides
    Fleury-Bregeot, Nicolas
    Oehlrich, Daniel
    Rombouts, Frederik
    Molander, Gary A.
    ORGANIC LETTERS, 2013, 15 (07) : 1536 - 1539
  • [2] A highly active catalytic system for Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
    Mao, Shu-Lan
    Sun, Yue
    Yu, Guang-Ao
    Zhao, Cui
    Han, Zhi-Jun
    Yuan, Jia
    Zhu, Xiaolei
    Yang, Qihua
    Liu, Sheng-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (47) : 9410 - 9417
  • [3] Suzuki-Miyaura Cross-Coupling Reactions of Primary Alkyltrifluoroborates with Aryl Chlorides
    Dreher, Spencer D.
    Lim, Siang-Ee
    Sandrock, Deidre L.
    Molander, Gary A.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3626 - 3631
  • [4] Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
    Molander, Gary A.
    Brown, Adam R.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9681 - 9686
  • [5] Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides
    Jabeen, S.
    Khera, R. A.
    Iqbal, J.
    Asgher, M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (09) : 1416 - 1422
  • [6] Synthesis of Triazole Click Ligands for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides
    S. Jabeen
    R. A. Khera
    J. Iqbal
    M. Asgher
    Russian Journal of Organic Chemistry, 2019, 55 : 1416 - 1422
  • [7] Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides
    Zhou, Tongliang
    Xie, Pei-Pei
    Ji, Chong-Lei
    Hong, Xin
    Szostak, Michal
    ORGANIC LETTERS, 2020, 22 (16) : 6434 - 6440
  • [8] Aryl and heteroaryl nosylates as stable and cheap partners for Suzuki-Miyaura cross-coupling reactions
    Dikova, Anna
    Cheval, Nicolas P.
    Blanc, Aurelien
    Weibel, Jean-Marc
    Pale, Patrick
    TETRAHEDRON, 2016, 72 (16) : 1960 - 1968
  • [9] Tetrabutylammonium 2-Pyridyltriolborate Salts for Suzuki-Miyaura Cross-Coupling Reactions with Aryl Chlorides
    Sakashita, Shohei
    Takizawa, Miho
    Sugai, Juugaku
    Ito, Hajime
    Yamamoto, Yasunori
    ORGANIC LETTERS, 2013, 15 (17) : 4308 - 4311
  • [10] Asymmetric Suzuki-Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover
    Kamei, Toshinori
    Sato, Akihiro H.
    Iwasawa, Tetsuo
    TETRAHEDRON LETTERS, 2011, 52 (21) : 2638 - 2641