Nickel nanoparticles supported on reduced graphene oxide sheets: a phosphine free, magnetically recoverable and cost effective catalyst for Sonogashira cross-coupling reactions

被引:49
作者
Hussain, Najrul [1 ,3 ]
Gogoi, Pranjal [2 ,3 ]
Khare, Puja [4 ]
Das, Manash R. [1 ,3 ]
机构
[1] North East Inst Sci & Technol, CSIR, Div Mat Sci, Jorhat 785006, Assam, India
[2] North East Inst Sci & Technol, CSIR, Div Med Chem, Jorhat 785006, Assam, India
[3] CSIR, Acad Sci & Innovat Res, New Delhi, India
[4] Cent Inst Med & Aromat Plants, CSIR, Agron & Soil Sci Div, Lucknow 226015, Uttar Pradesh, India
关键词
PD NANOPARTICLES; C-C; BIMETALLIC NANOPARTICLES; EFFICIENT CATALYST; REUSABLE CATALYST; GREEN SYNTHESIS; SUZUKI-MIYAURA; PALLADIUM; COMPOSITES; NANOSHEETS;
D O I
10.1039/c5ra22601e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this study, we have developed a cost effective and one-pot strategy for the synthesis of a heterogeneous catalyst consisting of a Ni nanoparticle-reduced graphene oxide composite for Sonogashira cross-coupling reactions. Several characterization tools were employed to characterize the Ni nanoparticle-reduced graphene oxide composite, which indicated that magnetic Ni nanoparticles of a size range of 1-4 nm were uniformly anchored on the reduced graphene oxide nanosheets without using any surfactant or stabilizing agent. Different types of aryl halides and phenylacetylenes were coupled under the optimized reaction conditions with excellent yields to give biphenylacetylenes. The ferromagnetic behaviour of the Ni nanoparticle-graphene composite resulted in it being easily separable from the reaction mixture and the composite was reusable, up to six times, without losing its catalytic activity. The fresh as well as the reused catalyst for the Sonogashira cross-coupling reaction was well characterized using analytical techniques which showed that the Ni nanoparticles were well dispersed on the reduced graphene oxide nanosheets without agglomeration, and the size and morphology of the catalyst remained unchanged after use in the catalytic reaction.
引用
收藏
页码:103105 / 103115
页数:11
相关论文
共 60 条
[31]   Pd-Partially Reduced Graphene Oxide Catalysts (Pd/PRGO): Laser Synthesis of Pd Nanoparticles Supported on PRGO Nanosheets for Carbon-Carbon Cross Coupling Reactions [J].
Moussa, Sherif ;
Siamaki, Ali R. ;
Gupton, B. Frank ;
El-Shall, M. Samy .
ACS CATALYSIS, 2012, 2 (01) :145-154
[32]   Palladium-catalyzed alkynylation [J].
Negishi, E ;
Anastasia, L .
CHEMICAL REVIEWS, 2003, 103 (05) :1979-2017
[33]   NiCl2•6H2O: an efficient catalyst precursor for phosphine-free Heck and Sonogashira cross-coupling reactions [J].
Nowrouzi, Najmeh ;
Zarei, Marjan .
TETRAHEDRON, 2015, 71 (41) :7847-7852
[34]   Palladium and Bimetallic Palladium-Nickel Nanoparticles Supported on Multiwalled Carbon Nanotubes: Application to CarbonCarbon Bond-Forming Reactions in Water [J].
Ohtaka, Atsushi ;
Sansano, Jose M. ;
Najera, Carmen ;
Miguel-Garcia, Izaskun ;
Berenguer-Murcia, Angel ;
Cazorla-Amoros, Diego .
CHEMCATCHEM, 2015, 7 (12) :1841-1847
[35]   Modulating Sonogashira Cross-Coupling Reactivity in Four-Coordinate Nickel Complexes by Using Geometric Control [J].
Petuker, Anette ;
Merten, Christian ;
Apfel, Ulf-Peter .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2015, (12) :2139-2144
[36]   Silica-supported palladium: Sustainable catalysts for cross-coupling reactions [J].
Polshettiwar, Vivek ;
Len, Christophe ;
Fihri, Aziz .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (21-22) :2599-2626
[37]   Enantioselective Synthesis of cis-1,2-Disubstituted Cyclopentanes and Cyclohexanes by Suzuki-Miyaura Cross-Coupling and Iridium-Catalyzed Asymmetric Hydrogenation [J].
Schumacher, Andreas ;
Schrems, Marcus G. ;
Pfaltz, Andreas .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) :13502-13509
[38]   Electrocatalytically Active Graphene-Platinum Nanocomposites. Role of 2-D Carbon Support in PEM Fuel Cells [J].
Seger, Brian ;
Kamat, Prashant V. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (19) :7990-7995
[39]   PdCo bimetallic nanoparticles supported on PPI-grafted graphene as an efficient catalyst for Sonogashira reactions [J].
Shaabani, Ahmad ;
Mahyari, Mojtaba .
JOURNAL OF MATERIALS CHEMISTRY A, 2013, 1 (32) :9303-9311
[40]   Synthesis, characterization and catalytic application of Au NPs-reduced graphene oxide composites material: an eco-friendly approach [J].
Sharma, Ponchami ;
Darabdhara, Gitashree ;
Reddy, Tallapareddy Muralikrishna ;
Borah, Ashwini ;
Bezboruah, Pranjal ;
Gogoi, Pranjal ;
Hussain, Najrul ;
Sengupta, Pinaki ;
Das, Manash R. .
CATALYSIS COMMUNICATIONS, 2013, 40 :139-144