Palladium-catalyzed Suzuki-Miyaura coupling with aryl and heteroaryl bromides using N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine

被引:17
|
作者
Wang, Kun [1 ]
Yi, Tao [1 ]
Yu, Xiaojun [1 ]
Zheng, Xueli [1 ]
Fu, Haiyan [1 ]
Chen, Hua [1 ]
Li, Ruixiang [1 ]
机构
[1] Sichuan Univ, Dept Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China
关键词
Suzuki-Miyaura coupling; palladium; tetraphosphine; HIGHLY EFFICIENT CATALYST; ARYLBORONIC ACIDS; HECK CATALYSIS; BORONIC ACIDS; COMPLEXES; TETRAPHOSPHINE; LIGAND; PHOSPHINE; HALIDES; SYSTEM;
D O I
10.1002/aoc.2869
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An easily prepared tetraphosphine N,N,N',N'-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (1) combined with PdCl2 affords an efficient catalytic system for Suzuki cross-coupling of aryl and heteroaryl bromides. A high turnover number of 750 000 is obtained with the catalyst loading as low as 1?ppm. This catalyst system exhibits good stability and longevity. In this study, a broad scope of substrates is investigated and satisfactory yields are obtained. Copyright (c) 2012 John Wiley & Sons, Ltd.
引用
收藏
页码:342 / 346
页数:5
相关论文
共 50 条
  • [1] N,N,N′,N′-tetra(diphenylphosphinomethyl)pyridine-2,6-diamine/palladium catalyzed Suzuki-Miyaura coupling of aryl and heteroaryl halides
    Guo, Fei-chen
    Zhou, Rong
    Jiang, Zhi-jie
    Wang, Wei
    Fu, Hai-yan
    Zheng, Xue-li
    Chen, Hua
    Li, Rui-xiang
    [J]. CATALYSIS COMMUNICATIONS, 2015, 66 : 87 - 90
  • [2] Heck coupling reaction catalyzed by [(C3H5)PdCl]2-N,N,N′,N′-tetra (diphenylphosphinomethyl)-1,2-ethylenediamine
    Yu, Xiao-Jun
    Zhou, Rong
    Zhang, Yu
    Fu, Hai-Yan
    Li, Rui-Xiang
    Chen, Hua
    Li, Xian-Jun
    [J]. CATALYSIS COMMUNICATIONS, 2010, 12 (03) : 222 - 225
  • [3] Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters
    Ben Halima, Taoufik
    Zhang, Wanying
    Yalaoui, Imane
    Hong, Xin
    Yang, Yun-Fang
    Houk, Kendall N.
    Newman, Stephen G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) : 1311 - 1318
  • [4] Palladium-catalyzed Suzuki-Miyaura reaction using saturated N-heterocarbene ligands
    Özdemir, I
    Çetinkaya, B
    Demir, S
    Gürbüz, N
    [J]. CATALYSIS LETTERS, 2004, 97 (1-2) : 37 - 40
  • [5] Synthesis of [n]- and [n.n]cyclophanes by using Suzuki-Miyaura coupling
    Smith, BB
    Hill, DE
    Cropp, TA
    Walsh, RD
    Cartrette, D
    Hipps, S
    Shachter, AM
    Pennington, WT
    Kwochka, WR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15): : 5333 - 5337
  • [6] 2-Pyridylquinoxaline derivatives as N,N-ligands for palladium-catalyzed Suzuki-Miyaura reaction
    Liu, Yundong
    Wu, Yongwei
    Xi, Chanjuan
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (08) : 329 - 332
  • [7] A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8059 - 8063
  • [8] Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
    Song, C
    Ma, YD
    Chai, Q
    Ma, CQ
    Jiang, W
    Andrus, MB
    [J]. TETRAHEDRON, 2005, 61 (31) : 7438 - 7446
  • [9] Palladium-Catalyzed C-N Cross-Coupling of N′-Monosubstituted Sulfondiimines with Aryl Bromides
    Candy, Mathieu
    Bohmann, Rebekka Anna
    Bolm, Carsten
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (16) : 2928 - 2932
  • [10] Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids
    Wang, Zhan-Yong
    Ma, Qin-Na
    Li, Ren-Hao
    Shao, Li-Xiong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (45) : 7899 - 7906