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
[1]   Copper-free Sonogashira Coupling Reaction Using a trans-Spanning 1,2-Bis(2-thienylethynyl)benzene Ligand [J].
Atobe, Shingo ;
Sonoda, Motohiro ;
Suzuki, Yuki ;
Shinohara, Hiroyuki ;
Yamamoto, Takuya ;
Ogawa, Akiya .
CHEMISTRY LETTERS, 2011, 40 (09) :925-927
[2]   Recent progress and current applications of Sonogashira coupling reaction in water [J].
Bakherad, Mohammad .
APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) :125-140
[3]   Nickel-Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Mihanparast, Samira .
SYNTHETIC COMMUNICATIONS, 2010, 40 (02) :179-185
[4]   Pd nanoparticles for C-C coupling reactions [J].
Balanta, Angelica ;
Godard, Cyril ;
Claver, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4973-4985
[5]   The nickel-catalyzed Sonogashira-Hagihara reaction [J].
Beletskaya, IP ;
Latyshev, GV ;
Tsvetkov, AV ;
Lukashev, NV .
TETRAHEDRON LETTERS, 2003, 44 (27) :5011-5013
[6]   One-pot preparation of Ni-graphene hybrids with enhanced catalytic performance [J].
Chen, Guiqiang ;
Wang, Fengli ;
Liu, Fei ;
Zhang, Xiao .
APPLIED SURFACE SCIENCE, 2014, 316 :568-574
[7]   Fast synthesis of Ag-Pd@reduced graphene oxide bimetallic nanoparticles and their applications as carbon-carbon coupling catalysts [J].
Chen, Mingxi ;
Zhang, Zhe ;
Li, Lingzhi ;
Liu, Yu ;
Wang, Wei ;
Gao, Jianping .
RSC ADVANCES, 2014, 4 (58) :30914-30922
[8]   Composites of Aminodextran-Coated Fe3O4 Nanoparticles and Graphene Oxide for Cellular Magnetic Resonance Imaging [J].
Chen, Weihong ;
Yi, Peiwei ;
Zhang, Yi ;
Zhang, Liming ;
Deng, Zongwu ;
Zhang, Zhijun .
ACS APPLIED MATERIALS & INTERFACES, 2011, 3 (10) :4085-4091
[9]   Graphene-supported metal/metal oxide nanohybrids: synthesis and applications in heterogeneous catalysis [J].
Cheng, Yi ;
Fan, Yiqiu ;
Pei, Yan ;
Qiao, Minghua .
CATALYSIS SCIENCE & TECHNOLOGY, 2015, 5 (08) :3903-3916
[10]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922