An Aerobic and Very Fast Pd/C-Catalyzed Ligand-Free and Aqueous Suzuki Reaction Under Mild Conditions

被引:52
作者
Liu, Chun [1 ]
Rao, Xiaofeng [1 ]
Zhang, Yixia [1 ]
Li, Xinmin [1 ]
Qiu, Jieshan [1 ]
Jin, Zilin [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Linggong Rd 2, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
Cross-coupling; Heterogeneous catalysis; Palladium; Biaryls; Liquid crystals; CROSS-COUPLING REACTIONS; HETEROGENEOUS PALLADIUM CATALYSTS; FLUORINATED LIQUID-CRYSTALS; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; MIYAURA REACTION; ARYL CHLORIDES; ORGANOBORON COMPOUNDS; HIGHLY EFFICIENT; VERSATILE METHOD;
D O I
10.1002/ejoc.201300334
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An aerobic, ligand-free Suzuki reaction catalyzed by Pd/C in aqueous media has been developed. This method is a very simple, efficient and mild protocol for the cross-coupling of aryl bromides with arylboronic acids, and the reactions proceeded smoothly in excellent yields within short reaction times. Control experiments demonstrated that the Pd/C-catalyzed Suzuki reaction was much quicker when performed in air or oxygen than in nitrogen. Furthermore, this protocol could be used for the synthesis of fluorinated liquid-crystalline compounds. The Pd/C catalyst could be recovered and recycled efficiently at least ten times without significant loss of catalytic activity.
引用
收藏
页码:4345 / 4350
页数:6
相关论文
共 84 条
  • [1] Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex
    Adamo, Carlo
    Amatore, Christian
    Ciofini, Ilaria
    Jutand, Anny
    Lakmini, Hakim
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6829 - 6836
  • [2] [Anonymous], ANGEW CHEM
  • [3] [Anonymous], 2012, ANGEW CHEM, V124, P5150
  • [4] A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants
    Arcadi, A
    Cerichelli, G
    Chiarini, M
    Correa, M
    Zorzan, D
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) : 4080 - 4086
  • [5] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions
    Arpad Molnar
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 2251 - 2320
  • [6] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view
    Astruc, Didier
    [J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1884 - 1894
  • [7] Pd nanoparticles for C-C coupling reactions
    Balanta, Angelica
    Godard, Cyril
    Claver, Carmen
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4973 - 4985
  • [8] The Suzuki coupling of aryl chlorides in TBAB-water mixtures
    Bedford, RB
    Blake, ME
    Butts, CP
    Holder, D
    [J]. CHEMICAL COMMUNICATIONS, 2003, (04) : 466 - 467
  • [9] Unexpected multifunctional effects of methylated cyclodextrins in a palladium charcoal-catalyzed Suzuki-Miyaura reaction
    Cassez, Andy
    Ponchel, Anne
    Hapiot, Frederic
    Monflier, Eric
    [J]. ORGANIC LETTERS, 2006, 8 (21) : 4823 - 4826
  • [10] Christ- mann U, 2005, ANGEW CHEM, V117, P370