Salicylaldoxime-functionalized poly(ethylene glycol)-bridged dicationic ionic liquid ([salox-PEG1000-DIL][BF4]) as a novel ligand for palladium-catalyzed Suzuki-Miyaura reaction in water

被引:25
作者
Wang, Yinglei [1 ]
Luo, Jun [1 ]
Liu, Zuliang [1 ]
机构
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
salicylaldoxime; poly(ethylene glycol); functionalized ionic liquid; Suzuki-Miyaura reaction; water; RECYCLABLE CATALYST; COUPLING REACTIONS; MAGNETIC NANOPARTICLE; RECOVERABLE CATALYST; HIGHLY EFFICIENT; N-ARYLATION; COMPLEX; PEG;
D O I
10.1002/aoc.3038
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Two novel salicylaldoxime-functionalized poly(ethylene glycol)-bridged dicationic ionic liquids ([salox-PEG1000-DIL][BF4] and [salox-PEG1000-DIL][PF6]) were prepared and characterized. [salox-PEG1000-DIL][BF4] was found to be an efficient and recyclable ligand for palladium-catalyzed Suzuki-Miyaura reaction in water. The catalytic system could be easily recovered and reused for at least five runs only with slight decrease in its activity. Copyright (c) 2013 John Wiley & Sons, Ltd.
引用
收藏
页码:601 / 605
页数:5
相关论文
共 52 条
[1]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].
Alonso, Francisco ;
Beletskaya, Irina P. ;
Yus, Miguel .
TETRAHEDRON, 2008, 64 (14) :3047-3101
[2]   Biguanide/Pd(OAc)2 immobilized on magnetic nanoparticle as a recyclable catalyst for the heterogeneous Suzuki reaction in aqueous media [J].
Beygzadeh, M. ;
Alizadeh, A. ;
Khodaei, M. M. ;
Kordestani, D. .
CATALYSIS COMMUNICATIONS, 2013, 32 :86-91
[3]  
Chaudhuri P, 1999, P INDIAN AS-CHEM SCI, V111, P397
[4]   Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].
Chen, J ;
Spear, SK ;
Huddleston, JG ;
Rogers, RD .
GREEN CHEMISTRY, 2005, 7 (02) :64-82
[5]   Microwave-Promoted Suzuki-Miyaura Cross-Coupling of Aryl Imidazolylsulfonates in Water [J].
Civicos, Jose F. ;
Alonso, Diego A. ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (14-15) :2771-2776
[6]   PEG as an alternative reaction medium in metal-mediated transformations [J].
Colacino, Evelina ;
Martinez, Jean ;
Lamaty, Frederic ;
Patrikeeva, Lyudmila S. ;
Khemchyan, Levon L. ;
Ananikov, Valentine P. ;
Beletskaya, Irina P. .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (23-24) :2893-2920
[7]   [Pd(HQS)2] (HQS=8-hydroxyquinoline-5-sulfonic acid) a highly efficient catalyst for Suzuki-Miyaura cross couplings in water [J].
Conelly-Espinosa, Patricia ;
Morales-Morales, David .
INORGANICA CHIMICA ACTA, 2010, 363 (06) :1311-1315
[8]   Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622
[9]   A general and mild Ullmann-type synthesis of diaryl ethers [J].
Cristau, HJ ;
Cellier, PP ;
Hamada, S ;
Spindler, JF ;
Taillefer, M .
ORGANIC LETTERS, 2004, 6 (06) :913-916
[10]   Mild conditions for copper-catalysed N-arylation of pyrazoles [J].
Cristau, HJ ;
Cellier, PP ;
Spindler, JF ;
Taillefer, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709