Novel robust benzimidazolylidene palladium complexes: synthesis, structure, and catalytic applications in amination of chloroarenes

被引：44
作者：
Fang, Weiwei [1 ]
Jiang, Jian [1 ]
Xu, Yong [1 ]
Zhou, Juefei [1 ]
Tu, Tao [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源：
TETRAHEDRON | 2013年 / 69卷 / 02期
基金：
中国国家自然科学基金;
关键词：
Amination; Benzimidazoles; Carbenes; Chloroarenes; Palladium; N-HETEROCYCLIC CARBENES; AGGREGATION;
D O I：
10.1016/j.tet.2012.11.003
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of novel pyridine stabilized Pd-NHC complexes were developed, which revealed high activities and broad substrates tolerance in the amination of various (hetero)-aryl chlorides. Besides various secondary amines, a wide range of primary anilines and aliphatic amines were also well tolerated. The results highlight us a new strategy to increase catalyst activity in the future catalyst design by alternating the sigma-donor property and flexibility of NHC ligands. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：673 / 679
页数：7
相关论文
共 40 条
  • [1] C-F Bond Activation in Organic Synthesis
    Amii, Hideki
    Uneyama, Kenji
    [J]. CHEMICAL REVIEWS, 2009, 109 (05) : 2119 - 2183
  • [2] [Anonymous], 2012, ADV SYNTH CATAL, V354, P1356
  • [3] A STABLE CRYSTALLINE CARBENE
    ARDUENGO, AJ
    HARLOW, RL
    KLINE, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 361 - 363
  • [4] Synthetic Routes to N-Heterocyclic Carbene Precursors
    Benhamou, Laure
    Chardon, Edith
    Lavigne, Guy
    Bellemin-Laponnaz, Stephane
    Cesar, Vincent
    [J]. CHEMICAL REVIEWS, 2011, 111 (04) : 2705 - 2733
  • [5] Sulfur-functionalized N-heterocyclic carbenes and their transition metal complexes
    Bierenstiel, Matthias
    Cross, Edward D.
    [J]. COORDINATION CHEMISTRY REVIEWS, 2011, 255 (5-6) : 574 - 590
  • [6] Stable carbenes
    Bourissou, D
    Guerret, O
    Gabbaï, FP
    Bertrand, G
    [J]. CHEMICAL REVIEWS, 2000, 100 (01) : 39 - 91
  • [7] de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
  • [8] N-Heterocyclic Carbenes in Late Transition Metal Catalysis
    Diez-Gonzalez, Silvia
    Marion, Nicolas
    Nolan, Steven P.
    [J]. CHEMICAL REVIEWS, 2009, 109 (08) : 3612 - 3676
  • [9] N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union
    Fortman, George C.
    Nolan, Steven P.
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5151 - 5169
  • [10] Heterocyclic carbenes: Synthesis and coordination chemistry
    Hahn, F. Ekkehardt
    Jahnke, Mareike C.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (17) : 3122 - 3172
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