Novel PEPPSI-Type NHC Pd(II) Metallosurfactants on the Base of 1H-Imidazole-4,5-dicarboxylic Acid: Synthesis and Catalysis in Water-Organic Media

被引:7
作者
Burilov, Vladimir [1 ]
Radaev, Dmitriy [1 ]
Sultanova, Elza [1 ]
Mironova, Diana [1 ]
Duglav, Daria [1 ]
Evtugyn, Vladimir [2 ]
Solovieva, Svetlana [3 ]
Antipin, Igor [1 ]
机构
[1] Kazan Fed Univ, 18 Kremlevskaya St, Kazan 420008, Russia
[2] Kazan Fed Univ, Interdisciplinary Ctr Analyt Microscopy, 18 Kremlevskaya St, Kazan 420008, Russia
[3] RAS, Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, 8 Arbuzov Str, Kazan 420008, Russia
基金
俄罗斯科学基金会;
关键词
PEPPSI complex; NHC; aggregation; p-nitrophenol reduction; Suzuki-Miyaura coupling; PRECATALYST ACTIVATION; NMR-SPECTROSCOPY; METAL-COMPLEXES; COORDINATION; INTERFACES; LIGANDS; AU(I);
D O I
10.3390/nano12224100
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carrying out organic reactions in water has attracted much attention. Catalytic reactions in water with metallosurfactants, which have both a metallocenter and the surface activity necessary for solubilizing hydrophobic reagents, are of great demand. Herein we proposed new approach to the synthesis of NHC PEPPSI metallosurfactants based on the sequential functionalization of imidazole 4,5-dicarboxylic acid with hydrophilic oligoethylene glycol and lipophilic alkyl fragments. Complexes of different lipophilicity were obtained, and their catalytic activity was studied in model reduction and Suzuki-Miyaura reactions. A comparison was made with the commercial PEPPSI-type catalytic systems designed by Organ. It was found that the reduction reaction in an aqueous solution of the metallosurfactant with the tetradecyl lipophilic fragment was three times more active than the commercially available PEPPSI complexes, which was associated with the formation of stable monodisperse aggregates detected by DLS and TEM.
引用
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页数:14
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