Magnetically recoverable catalysts based on mono- or bis-(NHC) complexes of palladium for the Suzuki-Miyaura reaction in aqueous media: two NHC-Pd linkages are better than one

被引:19
作者
Martinez-Olid, Francisco [1 ]
Andres, Roman [1 ]
de Jesus, Ernesto [1 ]
Flores, Juan C. [1 ]
Gomez-Sal, Pilar [1 ]
Heuze, Karine [2 ]
Vellutini, Luc [2 ]
机构
[1] Univ Alcala, Dept Quim Organ & Quim Inorgan, Campus Univ, Madrid 28871, Spain
[2] Univ Bordeaux, Inst Sci Mol, 351 Cours Liberat, F-33405 Talence, France
关键词
HETEROCYCLIC CARBENE COMPLEXES; RETRIEVABLE CATALYSTS; EFFICIENT CATALYSTS; NANOPARTICLES; ORGANOSILICA; SUPPORTS; HECK;
D O I
10.1039/c6dt01330a
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Pre-synthesized mono-and bis(NHC) palladium complexes have been grafted onto magnetic core/shell gamma-Fe2O3/silica particles and tested as catalysts in model Suzuki-Miyaura coupling reactions. The bis(NHC) immobilized complex was found to be a robust catalyst that can operate under mild conditions in aqueous media, even for the activation of chloroarene, whereas the mono(NHC) counterpart rapidly deactivates. Moreover, it can be readily recovered by magnetic separation and reused many times, providing very high productivities, and with so low leaching of palladium that the crude products obtained contain <= 10 ppm Pd.
引用
收藏
页码:11633 / 11638
页数:6
相关论文
共 39 条
[1]  
[Anonymous], 2013, PRACT ASP FUTUR DEV, DOI DOI 10.1002/9783527648283.CH3
[2]   Magnetically retrievable catalysts for asymmetric synthesis [J].
Baig, R. B. Nasir ;
Nadagouda, Mallikarjuna N. ;
Varma, Rajender S. .
COORDINATION CHEMISTRY REVIEWS, 2015, 287 :137-156
[3]   Magnetic Silica-Supported Palladium Catalyst: Synthesis of Allyl Aryl Ethers in Water [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2014, 53 (49) :18625-18629
[4]   Magnetically retrievable catalysts for organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL COMMUNICATIONS, 2013, 49 (08) :752-770
[5]  
Benaglia M., 2009, RECOVERABLE RECYCLAB
[6]   Recyclable Hybrid Silica-Based Catalysts Derived from Pd-NHC Complexes for Suzuki, Heck and Sonogashira Reactions [J].
Borja, Guadalupe ;
Monge-Marcet, Amalia ;
Pleixats, Roser ;
Parella, Teodor ;
Cattoen, Xavier ;
Man, Michel Wong Chi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (19) :3625-3635
[7]   Magnetically recoverable nanoparticles as efficient catalysts for organic transformations in aqueous medium [J].
Cheng, Tanyu ;
Zhang, Dacheng ;
Li, Hexing ;
Liu, Guohua .
GREEN CHEMISTRY, 2014, 16 (07) :3401-3427
[8]   Control of wettability by anion exchange on Si/SiO2 surfaces [J].
Chi, YS ;
Lee, JK ;
Lee, S ;
Choi, IS .
LANGMUIR, 2004, 20 (08) :3024-3027
[9]   Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554
[10]   Palladium-Catalysed Coupling Reactions [J].
de Vries, Johannes G. .
ORGANOMETALLICS AS CATALYSTS IN THE FINE CHEMICAL INDUSTRY, 2012, 42 :1-34