Efficient N-heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids

被引:15
|
作者
Liu, Xi-Yu [1 ]
Zhu, Hai-Bo [1 ]
Shen, Ya-Jing [1 ]
Jiang, Jian [1 ]
Tu, Tao [1 ,2 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金; 国家教育部博士点专项基金资助;
关键词
N-Heterocyclic carbene; Nickel; Cross coupling; Benzylic ammonium salts; Boronic acid; MOLECULAR-MASS GELATORS; ARYLBORONIC ACIDS; STEREOSPECIFIC FORMATION; GRIGNARD-REAGENTS; BOND ACTIVATION; AGGREGATION; HALIDES; RECOGNITION; PHOSPHATES; ALCOHOLS;
D O I
10.1016/j.cclet.2016.09.006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pyridine-bridged bis-benzimidazolylidene nickel complexes exhibited very high catalytic activity toward cross coupling of inactive (hetero)aryl benzylic ammonium salts with (hetero)aryl and alkenyl boronic acids under mild reaction conditions. Even at 2 mol% catalyst loading, a wide range of substrates for both coupling partners with different steric and electronic properties were well tolerated. (C) 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:350 / 353
页数:4
相关论文
共 50 条
  • [31] N-Heterocyclic Carbene Dirhodium(II) Complexes as Catalysts for Allylic and Benzylic Oxidations
    Coelho, Jaime A. S.
    Trindade, Alexandre F.
    Wanke, Riccardo
    Rocha, Bruno G. M.
    Veiros, Luis F.
    Gois, Pedro M. P.
    Pombeiro, Armando J. L.
    Afonso, Carlos A. M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (08) : 1471 - 1478
  • [32] Nickel N-heterocyclic carbene complexes and their utility in homogeneous catalysis
    Prakasham, A. P.
    Ghosh, Prasenjit
    INORGANICA CHIMICA ACTA, 2015, 431 : 61 - 100
  • [33] Nickel/N-Heterocyclic Carbene Catalysis Catalyzed Enantioselective Suzuki-Miyaura Coupling of Ketones
    Kong, Weiyu
    Yin, Guoyin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1751 - 1752
  • [34] Nickel N-heterocyclic carbene complexes in the vinyl polymerization of norbornene
    Berding, Joris
    Lutz, Martin
    Spek, Anthony L.
    Bouwman, Elisabeth
    APPLIED ORGANOMETALLIC CHEMISTRY, 2011, 25 (01) : 76 - 81
  • [35] Pincer N-heterocyclic carbene complexes of rhodium functionalised with pyridyl and bipyridyl donors
    Wright, Joseph A.
    Danopoulos, Andreas A.
    Motherwell, William B.
    Carroll, Robert J.
    Ellwood, Simon
    Sassmannshausen, Joerg
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (23) : 4857 - 4865
  • [36] Dihydroperimidine-Derived PNP Pincer Complexes as Intermediates en Route to N-Heterocyclic Carbene Pincer Complexes
    Hill, Anthony F.
    McQueen, Caitlin M. A.
    ORGANOMETALLICS, 2014, 33 (08) : 1909 - 1912
  • [37] N-Heterocyclic Carbene (NHC)-Pd Complexes: Industrially Applicable Cross Coupling Catalysts
    Horiguchi, Yoshiaki
    Nolan, Steven P.
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2009, 67 (06) : 653 - 655
  • [38] Metal complexes with 'pincer'-type ligands incorporating N-heterocyclic carbene functionalities
    Pugh, David
    Danopoulos, Andreas A.
    COORDINATION CHEMISTRY REVIEWS, 2007, 251 (5-6) : 610 - 641
  • [39] Nickel(II) complexes of bidentate N-heterocyclic carbene/phosphine ligands: Efficient catalysts for Suzuki coupling of aryl chlorides
    Lee, Chun-Chin
    Ke, Wei-Chi
    Chan, Kai-Ting
    Lai, Chun-Liang
    Hu, Ching-Han
    Lee, Hon Man
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (02) : 582 - 591
  • [40] Efficient synthesis of triarylamines catalyzed by palladium/N-heterocyclic carbene
    Chen, Chen
    Li, Ying-Feng
    Yang, Lian-Ming
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 269 (1-2) : 158 - 162