Recyclable ionic liquid-bridged chiral dimeric salen Mn(III) complexes for oxidative kinetic resolution of racemic secondary alcohols

被引：18
作者：
Li, Chengyong [1 ]
Zhao, Jiangfeng [1 ]
Tan, Rong [1 ]
Peng, Zhigang [1 ]
Luo, Rongchang [1 ]
Peng, Ming [1 ]
Yin, Donghong [1 ,2 ]
机构：
[1] Hunan Normal Univ, Inst Fine Catalysis & Synth, Changsha 410081, Hunan, Peoples R China
[2] China Tobacco Hunan Ind Corp, R&D Ctr, Changsha 410014, Hunan, Peoples R China
来源：
CATALYSIS COMMUNICATIONS | 2011年 / 15卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Chiral dimeric salen Mn(III) complexes; Ionic liquids (ILs); Catalysis; Secondary alcohols; Oxidative kinetic resolution; MOLECULAR-OXYGEN; CATALYSTS; EPOXIDATION; MECHANISM; SILICA;
D O I：
10.1016/j.catcom.2011.08.009
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Novel chiral dimeric salen Mn(III) complexes bridged with N,N-dialkylimidazolium ionic liquids (ILs) at the C-5 position of the salicylaldehyde moieties were designed and synthesized. The Its-bridged complexes presented excellent enantioselectivity and catalytic activity in the oxidative kinetic resolution of a-methyl benzyl alcohol, using diacetoxyiodobenzene as oxidant. The complexes combined the high catalytic efficiency of the active centers and the special solubility of the ILs, thus exhibiting notable efficacy of oxidative kinetic resolution and facile recovery from the reaction system by changing the solvent. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码：27 / 31
页数：5
相关论文
共 17 条
  • [1] Mechanism of the Enantioselective Oxidation of Racemic Secondary Alcohols Catalyzed by Chiral Mn(III)-Salen Complexes
    Brown, M. Kevin
    Blewett, Megan M.
    Colombe, James R.
    Corey, E. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) : 11165 - 11170
  • [2] The palladiuim-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen
    Ferreira, EM
    Stoltz, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (31) : 7725 - 7726
  • [3] A practical one-pot synthesis of enantiopure unsymmetrical salen ligands
    Holbach, M
    Zheng, XL
    Burd, C
    Jones, CW
    Weck, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (07) : 2903 - 2906
  • [4] Palladium-catalyzed enantioselective oxidations of alcohols using molecular oxygen
    Jensen, DR
    Pugsley, JS
    Sigman, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) : 7475 - 7476
  • [5] Environment friendly protocol for enantioselective epoxidation of non-functionalized alkenes catalyzed by recyclable homochiral dimeric Mn(III) salen complexes with hydrogen peroxide and UHP adduct as oxidants
    Kureshy, RI
    Singh, S
    Khan, NH
    Abdi, SHR
    Ahmed, I
    Bhatt, A
    Jasra, RV
    [J]. CATALYSIS LETTERS, 2006, 107 (1-2) : 127 - 130
  • [6] Easily recyclable chiral polymeric Mn(III) salen complexes for oxidative kinetic resolution of racemic secondary alcohols
    Kureshy, Rukhsana I.
    Ahmad, Irshad
    Pathak, Kavita
    Khan, Noor-Ul H.
    Abdi, Sayed H. R.
    Prathap, Jaya K.
    Jasra, Raksh V.
    [J]. CHIRALITY, 2007, 19 (05) : 352 - 357
  • [7] Kinetic resolution of racemic secondary alcohols catalyzed by chiral diaminodiphosphine-Ir(I) complexes
    Li, Yan-Yun
    Zhang, Xue-Qin
    Dong, Zhen-Rong
    Shen, Wei-Yi
    Chen, Gui
    Gao, Jing-Xing
    [J]. ORGANIC LETTERS, 2006, 8 (24) : 5565 - 5567
  • [8] Insight into the mechanism of oxidative kinetic resolution of racemic secondary alcohols by using manganese(III) (salen) complexes as catalysts
    Li, Z
    Tang, ZH
    Hu, XX
    Xia, CG
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (04) : 1210 - 1216
  • [9] Catalytic asymmetric and chemoselective aerobic oxidation: kinetic resolution of sec-alcohols
    Masutani, K
    Uchida, T
    Irie, R
    Katsuki, T
    [J]. TETRAHEDRON LETTERS, 2000, 41 (26) : 5119 - 5123
  • [10] Oxidative kinetic resolution of racemic secondary alcohols catalyzed by recyclable chiral dimeric Mn(III) salen catalysts
    Pathak, Kavita
    Ahmad, Irshad
    Abdi, Sayed H. R.
    Kureshy, Rukhsana I.
    Khan, Noor-ul H.
    Jasra, Raksh V.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 274 (1-2) : 120 - 126
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