Palladium/tetraphosphine catalyzed suzuki cross-coupling of heteroarylboronic acids with aryl halides

被引：23
|
作者：
Kondolff, Isabelle [2 ,3 ]
Doucet, Henri [1 ]
Santelli, Maurice [2 ,3 ]
机构：
[1] Univ Rennes Catalyse & Organomet, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France
[2] Univ Aix Marseille 3, Synth Organ Lab, Fac Sci St Jerome, Univ Aix Marseille 3 Chirotechnol Catalyse & Bioc, F-13397 Marseille 20, France
[3] Univ Aix Marseille 3, CNRS, UMR 6180, F-13397 Marseille 20, France
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 2008年 / 45卷 / 01期
关键词：
D O I：
10.1002/jhet.5570450109
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)](2) efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- orbenzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases, better results in terms of ratio substrate/catalyst were obtained for the reverse reaction using heteroaryl bromides with arylboronic acids.
引用
收藏
页码：109 / 118
页数：10
相关论文
共 50 条
  • [41] Palladium-Catalyzed Cross-Coupling of 2,3-Naphthoxadisilole with Aryl Halides
    Ding, Han
    Chen, Yali
    Cao, Weiguo
    Wu, Kaicheng
    Chen, Jie
    Lee, Albert W. M.
    SYNTHETIC COMMUNICATIONS, 2010, 40 (07) : 984 - 991
  • [42] An efficient catalyst system for palladium(0)-catalyzed cross-coupling of aryltrialkoxysilanes with aryl halides
    Murata, M
    Yoshida, S
    Nirei, S
    Watanabe, S
    Masuda, Y
    SYNLETT, 2006, (01) : 118 - 120
  • [43] ORGN 633-Palladium-catalyzed cross-coupling of heterocyclic silanolates with aryl halides
    Denmark, Scott E.
    Baird, John D.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [44] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF HETEROARYLTRIOLBORATES WITH ARYL HALIDES FOR SYNTHESIS OF BIARYLS
    Yamamoto, Yasunori
    Takizawa, Miho
    Yu, Xiao-Qiang
    Miyaura, Norio
    HETEROCYCLES, 2010, 80 (01) : 359 - 368
  • [45] Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Aryl Halides Under Mild Conditions
    Rosa, David
    Orellana, Arturo
    ORGANIC LETTERS, 2011, 13 (01) : 110 - 113
  • [46] Palladium-tetraphosphine complex: An efficient catalyst for allylic substitution and Suzuki cross-coupling
    Feuerstein, M
    Laurenti, D
    Doucet, H
    Santelli, M
    SYNTHESIS-STUTTGART, 2001, (15): : 2320 - 2326
  • [47] Palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with aryl triflates
    Yao, ML
    Deng, MZ
    SYNTHESIS-STUTTGART, 2000, (08): : 1095 - 1100
  • [48] An efficient and reusable polymer-supported palladium catalyst for the Suzuki cross-coupling reactions of aryl halides
    Islam, S. M.
    Mondal, P.
    Roy, A. Singha
    Mondal, S.
    Mobarak, M.
    JOURNAL OF CHEMICAL RESEARCH, 2009, (12) : 756 - 760
  • [49] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols
    Arentsen, K
    Caddick, S
    Geoffrey, F
    Cloke, N
    Herring, AP
    Hitchcock, PB
    TETRAHEDRON LETTERS, 2004, 45 (17) : 3511 - 3515
  • [50] Indazolium halides as efficient ligands for Pd-catalyzed Suzuki-Miyaura cross-coupling of aryl bromides with arylboronic acids
    Chen, Qian
    Mao, Zhuqing
    Guo, Fang
    Liu, Xiaoshuang
    TETRAHEDRON LETTERS, 2016, 57 (33) : 3735 - 3738
12345