Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid

被引：3
|
作者：
Wang, Biyu [1 ]
Ni, Peizhong [1 ]
Fan, Jili [1 ]
Zheng, Huidong [1 ]
Zhao, Suying [1 ]
Bai, Zhengshuai [1 ,2 ]
机构：
[1] Fuzhou Univ, Sch Chem Engn, Fuzhou 350108, Peoples R China
[2] Fuzhou Univ, State Key Lab Photocatalysis Energy & Environm, Fuzhou 350002, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 34卷 / 12期
关键词：
Suzuki cross coupling reaction; pyridylboronic acid; aryl bromide; catalytic mechanism; SALEN; EPOXIDATION;
D O I：
10.6023/cjoc201407024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of 3-tert-butyl-2-hydroxy-5-(pyridin-4-yl)benzaldehyde by Suzuki cross coupling reaction of 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde with pyridin-4-ylboronic acid was studied by using different catalysts [Pd(dppf)(2)Cl-2, Pd(OAc)(2) and Pd(PPh3)(4)], bases (Na2CO3, NaHCO3, K2CO3, K3PO4, Cs2CO3 and CsF) and solvents (DME/H2O, DMF/H2O and dioxane/H2O) under different temperature of 70, 80 and 100 degrees C. A compatible method was developed for the coupling reaction of arylboronic acids (having electron donating or withdrawing group) with aryl bromides (having electron withdrawing group). Under the condition of Pd(PPh3)(4), K2CO3, dioxane/H2O (V : V=4 : 1), 80 degrees C, the yield is excellent (97%) and the product separation is easy. The compatibility for aryl bromides with electron donating group is moderate.
引用
收藏
页码：2471 / 2477
页数：7
相关论文
共 35 条
  • [1] Asymmetric catalysis of carbon-carbon bond-forming reactions using metal(salen) complexes
    Achard, TRJ
    Clutterbuck, LA
    North, M
    [J]. SYNLETT, 2005, (12) : 1828 - 1847
  • [2] OBSERVATION OF CATALYTIC INTERMEDIATES IN THE SUZUKI REACTION BY ELECTROSPRAY MASS-SPECTROMETRY
    ALIPRANTIS, AO
    CANARY, JW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) : 6985 - 6986
  • [3] Synthesis of new 8-arylisoquinoline derivatives by application of palladium-catalyzed Suzuki cross-coupling reactions
    Andreu, I
    Cabedo, N
    Fabis, F
    Cortes, D
    Rault, S
    [J]. TETRAHEDRON, 2005, 61 (34) : 8282 - 8287
  • [4] Chiral salen complexes: An overview to recoverable and reusable homogeneous and heterogeneous catalysts
    Baleizao, Carlos
    Garcia, Hermenegildo
    [J]. CHEMICAL REVIEWS, 2006, 106 (09) : 3987 - 4043
  • [5] Baranano D, 1997, CURR ORG CHEM, V1, P287
  • [6] Adsorptive stripping voltammetric behaviour of UO2(II) complexed with the Schiff base N,N′-ethylenebis(salicylidenimine) in aqueous 4-(2-hydroxyethyl)-1-piperazine ethanesulfonic acid medium
    Bastos, MBR
    Moreira, JC
    Farias, PAM
    [J]. ANALYTICA CHIMICA ACTA, 2000, 408 (1-2) : 83 - 88
  • [7] Cavazzini M, 2001, EUR J ORG CHEM, V2001, P4639
  • [8] Salen-Complex-Mediated Formation of Cyclic Carbonates by Cycloaddition of CO2 to Epoxides
    Decortes, Antonello
    Castilla, Ana M.
    Kleij, Arjan W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (51) : 9822 - 9837
  • [9] New practical syntheses of 4′-methylbiphenyl-2-carbonitrile and-2-carbaldehyde
    Goubet, D
    Meric, P
    Dormoy, JR
    Moreau, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4516 - 4518
  • [10] Homochiral Nickel Coordination Polymers Based on Salen(Ni) Metalloligands: Synthesis, Structure, and Catalytic Alkene Epoxidation
    Huang, Yuanbiao
    Liu, Tianfu
    Lin, Jingxiang
    Lue, Jian
    Lin, Zujin
    Cao, Rong
    [J]. INORGANIC CHEMISTRY, 2011, 50 (06) : 2191 - 2198
1234