Recent advances in mechanistic studies on Ni catalyzed cross-coupling reactions

被引:52
作者
Li, Zhe [1 ]
Liu, Lei [1 ]
机构
[1] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China
基金
国家高技术研究发展计划(863计划); 中国国家自然科学基金;
关键词
Nickel; Homogeneous catalysis; Cross-coupling; C-C bond formation; Mechanism; SECONDARY ALKYL BROMIDES; SUZUKI-MIYAURA REACTION; OXIDATIVE-ADDITION; NICKEL-COMPLEXES; ARYL ESTERS; STEREOSPECIFIC FORMATION; ROOM-TEMPERATURE; BOND ACTIVATION; HECK REACTIONS; BORONIC ACIDS;
D O I
10.1016/S1872-2067(14)60217-5
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A variety of Ni catalyzed cross-coupling reactions have emerged as efficient new methods for the construction of C-C bonds, and many mechanistic studies have been conducted to understand the factors controlling the reactivity and selectivity of Ni catalyzed reactions. The mechanisms of Ni catalyzed reactions are often very different from the corresponding Pd catalyzed processes because radical or bimetallic pathways are frequently involved in Ni catalyzed cross-coupling reactions. This review summarized recent advances in the mechanism of Ni catalyzed cross-coupling reactions. These are important for the development of new Ni catalyzed cross-coupling reactions with improved efficiency and selectivity. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:3 / 14
页数:12
相关论文
共 72 条
  • [1] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A
    Amaike, Kazuma
    Muto, Kei
    Yamaguchi, Junichiro
    Itami, Kenichiro
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13573 - 13576
  • [2] [Anonymous], 2009, Organotransition Metal Chemistry. From Bonding to Catalysis
  • [3] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides
    Biswas, Soumik
    Weix, Daniel J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) : 16192 - 16197
  • [4] Bimetallic Oxidative Addition Involving Radical Intermediates in Nickel-Catalyzed Alkyl-Alkyl Kumada Coupling Reactions
    Breitenfeld, Jan
    Ruiz, Jesus
    Wodrich, Matthew D.
    Hu, Xile
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (32) : 12004 - 12012
  • [5] Why Are (NN2)Ni Pincer Complexes Active for Alkyl-Alkyl Coupling: β-H Elimination Is Kinetically Accessible but Thermodynamically Uphill
    Breitenfeld, Jan
    Vechorkin, Oleg
    Corminboeuf, Clemence
    Scopelliti, Rosario
    Hu, Xile
    [J]. ORGANOMETALLICS, 2010, 29 (17) : 3686 - 3689
  • [6] Progress in organic reactions catalyzed by bimetallic nanomaterials
    Cai, Shuangfei
    Wang, Dingsheng
    Niu, Zhiqiang
    Li, Yadong
    [J]. CHINESE JOURNAL OF CATALYSIS, 2013, 34 (11) : 1964 - 1974
  • [7] Selected patented cross-coupling reaction technologies
    Corbet, Jean-Pierre
    Mignani, Gerard
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2651 - 2710
  • [8] Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C-O Bonds with Silanes: Ruling out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I) Intermediates
    Cornella, Josep
    Gomez-Bengoa, Enrique
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (05) : 1997 - 2009
  • [9] Nickel complexes of a pincer NN2 ligand:: Multiple carbon-chloride activation of CH2Cl2 and CHCl3 leads to selective carbon-carbon bond formation
    Csok, Zsolt
    Vechorkin, Oleg
    Harkins, Seth B.
    Scopelliti, Rosario
    Hu, Xile
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) : 8156 - +
  • [10] Exploring trifluoromethylation reactions at nickel: A structural and reactivity study
    Dubinina, Galyna G.
    Brennessel, William W.
    Miller, Jennifer L.
    Vicic, David A.
    [J]. ORGANOMETALLICS, 2008, 27 (15) : 3933 - 3938