A novel pyridine-bridged bis-benzimidazolylidene pincer palladium complex:: Synthesis and catalytic properties

被引：79
|
作者：
Tu, Tao [1 ]
Malineni, Jagadeesh [1 ]
Doetz, Karl Heinz [1 ]
机构：
[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 11-12期
关键词：
benzimidazoles; carbenes; Heck reaction; palladium; Suzuki coupling;
D O I：
10.1002/adsc.200800244
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A novel pyridine-bridged bis-benzimidazolylidene CNC pincer complex 1 was synthesized from cheap, commercially available precursors under microwave assistance in moderate yield. It catalyzes cross-coupling reactions of aryl halides with alkyl acrylates (Heck reaction) and phenylboronic acid (Suzuki reaction) under aerobic conditions with extremely high turn-over numbers (frequencies) indicating that a planar extension of the pi-system by henzannelation significantly increases the catalytic activity even with trace amounts of catalyst loading.
引用
收藏
页码：1791 / 1795
页数：5
相关论文
共 50 条
  • [1] A robust hydrophilic pyridine-bridged bis-benzimidazolylidene palladium pincer complex: Synthesis and its catalytic application towards Suzuki-Miyaura couplings in aqueous solvents
    Tu, Tao
    Feng, Xike
    Wang, Zhixun
    Liu, Xiyu
    DALTON TRANSACTIONS, 2010, 39 (44) : 10598 - 10600
  • [2] A pyridine-bridged bis-benzimidazolylidene pincer nickel(II) complex: synthesis and practical catalytic application towards Suzuki-Miyaura coupling with less-activated electrophiles
    Tu, Tao
    Mao, Han
    Herbert, Christian
    Xu, Mizhi
    Doetz, Karl Heinz
    CHEMICAL COMMUNICATIONS, 2010, 46 (41) : 7796 - 7798
  • [3] Efficient Air-Stable Organometallic Low-Molecular-Mass Gelators for Ionic Liquids: Synthesis, Aggregation and Application of Pyridine-Bridged Bis(benzimidazolylidene)-Palladium Complexes
    Tu, Tao
    Bao, Xiaoling
    Assenmacher, Wilfried
    Peterlik, Herwig
    Daniels, Joerg
    Doetz, Karl Heinz
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (08) : 1853 - 1861
  • [4] Efficient Aqueous-Phase Heck Reaction Catalyzed by a Robust Hydrophilic Pyridine-Bridged Bisbenzimidazolylidene-Palladium Pincer Complex
    Wang, Zhixun
    Feng, Xike
    Fang, Weiwei
    Tu, Tao
    SYNLETT, 2011, (07) : 951 - 954
  • [5] Palladium pincer-type complexes and zwitterionic sulfur adducts of pyridine-bridged bis (1,2,3-triazolin-5-ylidenes): syntheses, characterizations and catalytic applications
    Wang, Haiying
    Zhang, Bo
    Yan, Xuechao
    Guo, Shuai
    DALTON TRANSACTIONS, 2018, 47 (02) : 528 - 537
  • [6] Organometallic polymers based on fluorene-bridged bis-benzimidazolylidene via direct ligand-metal coordination: synthesis, characterization and optical properties
    Wu, Chia-Shing
    Lee, Yung-Teng
    Chen, Yun
    POLYMER CHEMISTRY, 2012, 3 (10) : 2776 - 2784
  • [7] Synthesis and catalytic properties of novel polyfluorinated pincer palladium complexes.
    Jensen, MJ
    Kornienko, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U45 - U45
  • [8] Synthesis and structures of novel pyridine-bridged phanes of 4,4′-bipyridine
    Scheytza, H
    Rademacher, O
    Reissig, HU
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (09) : 2373 - 2381
  • [9] Methyl-palladium(II) complexes of pyridine-bridged bis(nucleophilic heterocyclic carbene) ligands: Substituent effects on structure, stability, and catalytic performance
    Nielsen, DJ
    Cavell, KJ
    Skelton, BW
    White, AH
    INORGANICA CHIMICA ACTA, 2006, 359 (06) : 1855 - 1869
  • [10] Synthesis of pyridine-bridged bisferrocene and its pH value adjustable photoelectric properties
    Ma, Jingjing
    Zhai, Yali
    Chen, Jiahui
    Zhou, Xiang
    Shi, Weimin
    Zhang, Jianye
    Li, Gaiping
    Hou, Hong Wei
    TETRAHEDRON, 2020, 76 (13)
12345