Pd/C-Catalyzed Highly Efficient and Green Suzuki Cross-Coupling Reaction

被引:6
|
作者
Chu, Wenyi [1 ,2 ]
Wang, Man [1 ,2 ]
Li, Xinmin [1 ,2 ]
Hou, Yanjun [1 ,2 ]
Sun, Zhizhong [1 ,2 ]
机构
[1] Heilongjiang Univ, Sch Chem & Mat Sci, Harbin 150080, Peoples R China
[2] Coll Heilongjiang Prov, Key Lab Chem Engn Proc & Technol Highefficiency C, Harbin 150080, Peoples R China
关键词
Pd/C; Suzuki reaction; biphenyls; ionic liquid; LIGAND-FREE; HETEROGENEOUS PALLADIUM; ARYLBORONIC ACIDS; ARYL; COMPLEXES; HALIDES; SONOGASHIRA; HETEROARYL; CHLORIDES; CARBON;
D O I
10.6023/cjoc201206029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient protocol for the Suzuki reaction catalyzed by Pd/C has been developed in a green sovent. This method is able to prepare a variety of biaryls in high yields. In the presence of 1-butyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide, the cross-coupling reaction of aryl bromides with arylboronic acids proceed smoothly in PEG400 aqueous at 45 degrees C. The catalyst could be recycled four times without loss of activity.
引用
收藏
页码:1666 / 1672
页数:7
相关论文
共 38 条
  • [1] Cobalt-Catalyzed Preparation of Arylindium Reagents from Aryl and Heteroaryl Bromides
    Adak, Laksmikanta
    Yoshikai, Naohiko
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (18): : 7563 - 7568
  • [2] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
    Billingsley, Kelvin
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) : 3358 - 3366
  • [3] Trinuclear copper(I) complex of 1,3-bis(2-pyridinylmethyl)imidazolylidene as a carbene-transfer reagent for the preparation of catalytically active nickel(II) and palladium(II) complexes
    Chen, Chao
    Qiu, Huayu
    Chen, Wanzhi
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 696 (26) : 4166 - 4172
  • [4] Pd-leaching and Pd-removal in Pd/C-catalyzed Suzuki couplings
    Chen, Jeng-Shiou
    Vasiliev, Aleksey N.
    Panarello, Anthony P.
    Khinast, Johannes G.
    [J]. APPLIED CATALYSIS A-GENERAL, 2007, 325 (01) : 76 - 86
  • [5] Self-supported thiourea-palladium complexes: Highly air-stable and recyclable catalysts for the Suzuki reaction in neat water
    Chen, Wei
    Li, Rui
    Wu, Yong
    Ding, Li-Sheng
    Chen, Ying-Chun
    [J]. SYNTHESIS-STUTTGART, 2006, (18): : 3058 - 3062
  • [6] Mild and ligand-free palladium-catalyzed cross-couplings between aryl halides and arylboronic acids for the synthesis of biaryls and heterocycle-containing biaryls
    Deng, Chen-Liang
    Guo, Sheng-Mei
    Xie, Ye-Xiang
    Li, Jin-Heng
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (09) : 1457 - 1462
  • [7] Pd/C: An old catalyst for new applications - Its use for the Suzuki-Miyaura reaction
    Felpin, Francois-Xavier
    Ayad, Tahar
    Mitra, Soumya
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (12) : 2679 - 2690
  • [8] Triphenylphosphine-mediated reductive cyclization of 2-nitrobiphenyls: A practical and convenient synthesis of carbazoles
    Freeman, AW
    Urvoy, M
    Criswell, ME
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13): : 5014 - 5019
  • [9] Hans M., 1967, CHEM BER, V100
  • [10] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction
    Hassan, J
    Sévignon, M
    Gozzi, C
    Schulz, E
    Lemaire, M
    [J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1359 - 1469