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

被引:39
|
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] 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
  • [2] 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
  • [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] 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
  • [5] 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
  • [6] 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
  • [7] 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
  • [8] Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water
    Kolychev, Eugene L.
    Asachenko, Andrey F.
    Dzhevakov, Pavel B.
    Bush, Alexander A.
    Shuntikov, Viacheslav V.
    Khrustalev, Victor N.
    Nechaev, Mikhail S.
    DALTON TRANSACTIONS, 2013, 42 (19) : 6859 - 6866
  • [9] Efficient Nickel Precatalysts for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions
    John, Morgan E.
    Nutt, Michael J.
    Offer, Josephine E.
    Duczynski, Jeremy A.
    Yamazaki, Ken
    Miura, Tomoya
    Moggach, Stephen A.
    Koutsantonis, George A.
    Dorta, Reto
    Stewart, Scott G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [10] Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
    Asano, Shigehiro
    Kamioka, Seiji
    Isobe, Yoshiaki
    TETRAHEDRON, 2012, 68 (01) : 272 - 279