Phosphine-free hydrazone-Pd complex as the catalyst precursor for a Suzuki-Miyaura reaction under mild aerobic conditions

被引:164
|
作者
Mino, T [1 ]
Shirae, Y [1 ]
Sakamoto, M [1 ]
Fujita, T [1 ]
机构
[1] Chiba Univ, Fac Engn, Dept Appl Chem & Biotechnol, Inage Ku, Chiba 2638522, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 06期
关键词
D O I
10.1021/jo048107i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Glyoxal bis(N-methyl-N-phenylhydrazone) (1) and its related compounds such as 2-pyridine-carboxaldehyde N-methyl-N-phenylhydrazone (3) were prepared and examined as ligands for the Suzuki-Miyaura cross-coupling reaction of aryl halides and arylboronic acids. We found phosphine-free catalysts, such as Pd(OAc)(2)/hydrazone ligand 1 or 3, to be efficient catalysts for a variety of substrates to produce the coupling products in good yields.
引用
收藏
页码:2191 / 2194
页数:4
相关论文
共 50 条
  • [1] Phosphine-free Suzuki-Miyaura reactions catalyzed by bishydrazone-Pd-complex
    Mino, T
    Shirae, Y
    Sakamoto, M
    Fujita, T
    SYNLETT, 2003, (06) : 882 - 884
  • [2] ORGN 270-Mild and phosphine-free Suzuki-Miyaura coupling reaction catalyzed by Pd/C
    Kitamura, Yoshiaki
    Sako, Satoko
    Udzu, Takahiro
    Sakurai, Ai
    Tanaka, Asami
    Kobayashi, Yusuke
    Bora, Utpal
    Kurita, Takanori
    Kozaki, Atsushi
    Maegawa, Tomohiro
    Sajiki, Hironao
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [3] Nickel and palladium nanocomposite carbon aerogels as recyclable catalysts for Suzuki-Miyaura reaction under aerobic and phosphine-free conditions in water
    Martin, Laura
    Molins, Elies
    Vallribera, Adelina
    TETRAHEDRON, 2012, 68 (32) : 6517 - 6520
  • [4] Atomically dispersed palladium catalyses Suzuki-Miyaura reactions under phosphine-free conditions
    Ding, Guodong
    Hao, Leiduan
    Xu, Haiping
    Wang, Liguang
    Chen, Jian
    Li, Tao
    Tu, Xinman
    Zhang, Qiang
    COMMUNICATIONS CHEMISTRY, 2020, 3 (01)
  • [5] Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine-free Suzuki reaction in water and copper-free Sonogashira reaction under aerobic conditions
    Mandegani, Zeinab
    Asadi, Mozaffar
    Asadi, Zahra
    APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (08) : 657 - 663
  • [6] Recyclable nickel catalysed Suzuki-Miyaura reaction in the presence of polyethyleneimine under phosphine-free conditions in ethylene glycol
    Goudarzian, Nooredin
    Gholinejad, Mohammad
    Ghahramani, Parisa
    JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (04) : 485 - 489
  • [7] Supported phosphine-free palladium catalysts for the Suzuki-Miyaura reaction in aqueous media
    Phan, Nam T. S.
    Styring, Peter
    GREEN CHEMISTRY, 2008, 10 (10) : 1055 - 1060
  • [8] An efficient catalyst for Suzuki-Miyaura coupling reaction in aqueous medium under aerobic conditions
    Chen, CL
    Liu, YH
    Peng, SM
    Liu, ST
    TETRAHEDRON LETTERS, 2005, 46 (03) : 521 - 523
  • [9] Ferrocenylimidazoline palladacycles: efficient phosphine-free catalysts for Suzuki-Miyaura cross-coupling reaction
    Ma, Ji
    Cui, Xiuling
    Zhang, Bi
    Song, Maoping
    Wu, Yangjie
    TETRAHEDRON, 2007, 63 (25) : 5529 - 5538
  • [10] Benzotriazole : An efficient, inexpensive and phosphine-free ligand for the palladium-catalyzed Suzuki-Miyaura reaction
    Jha, Rajeev Ranjan
    Chaudhary, Ritu
    Chandra, Ramesh
    Verma, Akhilesh Kumar
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2011, 88 (08) : 1187 - 1194