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
  • [11] Iolio A. B., 1997, ELECTROCHIM ACTA, V42, P2065
  • [12] Jesmin M., 2010, J PHARM SCI-US, V34, P20
  • [13] Catalytic Transesterifications by a Zn-BisSalen MOF Containing Open Pyridyl Groups Inside 1D Channels
    Kim, Wan-Seok
    Lee, Kyung Yeon
    Ryu, Eui-Hyun
    Gu, Ja-Min
    Kim, Youngmee
    Lee, Suk Joong
    Huh, Seong
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, 2013 (24) : 4228 - 4233
  • [14] Functionalized poly- and oligo-phenylenes: Variations on the Suzuki cross-coupling of functionalized aryl dibromides with the 1,3-propanediol diester of 2,5-dialkyl-1,4-phenylenediboronic acid
    Kowitz, C
    Wegner, G
    [J]. TETRAHEDRON, 1997, 53 (45) : 15553 - 15574
  • [15] Microwave-assisted intramolecular Suzuki-Miyaura reaction to macrocycle, a concise asymmetric total synthesis of biphenomycin B
    Lépine, R
    Zhu, JP
    [J]. ORGANIC LETTERS, 2005, 7 (14) : 2981 - 2984
  • [16] Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings
    Lu, Guo-Ping
    Voigtritter, Karl R.
    Cai, Chun
    Lipshutz, Bruce H.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08): : 3700 - 3703
  • [17] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORONIC ACIDS WITH ORGANIC ELECTROPHILES
    MARTIN, AR
    YANG, YH
    [J]. ACTA CHEMICA SCANDINAVICA, 1993, 47 (03): : 221 - 230
  • [18] Chromium- and manganese-salen promoted epoxidation of alkenes
    McGarrigle, EM
    Gilheany, DG
    [J]. CHEMICAL REVIEWS, 2005, 105 (05) : 1563 - 1602
  • [19] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
    MIYAURA, N
    SUZUKI, A
    [J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483
  • [20] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES
    MIYAURA, N
    YANAGI, T
    SUZUKI, A
    [J]. SYNTHETIC COMMUNICATIONS, 1981, 11 (07) : 513 - 519
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