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
  • [1] Efficient N-heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids
    Xi-Yu Liu
    Hai-Bo Zhu
    Ya-Jing Shen
    Jian Jiang
    Tao Tu
    Chinese Chemical Letters, 2017, 28 (02) : 350 - 353
  • [2] Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
    Guan, Pei
    Cao, Changsheng
    Liu, Yun
    Li, Yunfei
    He, Pan
    Chen, Qian
    Liu, Gang
    Shi, Yanhui
    TETRAHEDRON LETTERS, 2012, 53 (45) : 5987 - 5992
  • [3] Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel Complexes
    Guo, Wang-Jun
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03): : 1054 - 1061
  • [4] Cross coupling of benzylammonium salts with boronic acids using a well-defined N-heterocyclic carbene-palladium(ii) precatalyst
    Wang, Tao
    Guo, Jiarui
    Wang, Xiaojuan
    Guo, Han
    Jia, Dingli
    Wang, Hengjin
    Liu, Lantao
    RSC ADVANCES, 2019, 9 (10) : 5738 - 5741
  • [5] Carbon-Sulfur Coupling Reactions Catalyzed by Nickel(II) N-Heterocyclic Carbene Complexes
    Neshat, Abdollah
    Khezri, Rahimeh
    Yousefshahi, Mohammad Reza
    Gholinejad, Mohammad
    Varmaghani, Fahimeh
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2023, 26 (36)
  • [6] Reactivity studies of pincer protic N-heterocyclic carbene complexes of nickel, palladium, and platinum
    Marelius, David C.
    Darrow, Evan H.
    Moore, Curtis E.
    Rheingold, Arnold L.
    Grotjahn, Douglas B.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [7] N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts
    Kim, Inwon
    Im, Honggu
    Lee, Hyeonyeong
    Hong, Sungwoo
    CHEMICAL SCIENCE, 2020, 11 (12) : 3192 - 3197
  • [8] Research Progress on Pincer N-Heterocyclic Carbene Metal Complexes
    Yang, Liangru
    Guo, Mengli
    Yuan, Jinwei
    Wang, Jiamei
    Xia, Yuting
    Xiao, Yongmei
    Mao, Pu
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (06) : 2002 - 2025
  • [9] C-X (X = N, O) Cross-Coupling Reactions Catalyzed by Copper-Pincer Bis(N-Heterocyclic Carbene) Complexes
    Minnick, Jennifer L.
    Domyati, Doaa
    Ammons, Rachel
    Tahsini, Laleh
    FRONTIERS IN CHEMISTRY, 2019, 7
  • [10] Regioselective Allene Hydrosilylation Catalyzed by N-Heterocyclic Carbene Complexes of Nickel and Palladium
    Miller, Zachary D.
    Li, Wei
    Belderrain, Tomas R.
    Montgomery, John
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (41) : 15282 - 15285