Organic syntheses by microwave selective heating of novel metal/CMC catalysts - The Suzuki-Miyaura coupling reaction in toluene and the dehydrogenation of tetralin in solvent-free media

被引:14
作者
Horikoshi, Satoshi [1 ]
Suttisawat, Yindee [1 ]
Osawa, Atsushi [1 ,2 ]
Takayama, Chiemi [1 ]
Chen, Xiuqin [2 ]
Yang, Shaoming [2 ]
Sakai, Hideki [2 ]
Abe, Masahiko [2 ]
Serpone, Nick [3 ]
机构
[1] Sophia Univ, Fac Sci & Technol, Dept Mat & Life Sci, Chiyoda Ku, Tokyo 1028554, Japan
[2] Tokyo Univ Sci, Fac Sci & Technol, Dept Pure & Appl Chem, Noda, Chiba 2788510, Japan
[3] Univ Pavia, Dipartimento Chim, Grp Fotochim, I-27100 Pavia, Italy
基金
日本学术振兴会;
关键词
Carbon microcoils; Activated carbon; Hot spots; Microplasma; Microwaves; Suzuki-Miyaura coupling reaction; Tetralin dehydrogenation reaction;
D O I
10.1016/j.jcat.2012.02.019
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The present study examines carbon microcoils (CMCs) as a novel support for Pt and Pd nanocatalysts and compares it with activated carbon nanoparticles as support for Pt and Pd metal deposits in two model microwave-assisted organic syntheses: (i) the Suzuki-Miyaura coupling reaction between phenylboronic acid and 1-bromo-4-methylbenzene in toluene solvent to produce 4-methyl-biphenyl and (ii) the dehydrogenation of tetralin (1,2,3,4-tetrahydronaphthalene) in solvent-free conditions. The microwave absorption capacity of the CMCs was more effective than the ACs support from the viewpoint of dielectric parameters (dielectric constant, dielectric loss, and loss tangent). Possible generation of microplasma (i.e., hot spots) on both supports that can impact on the progress of the reactions was monitored visually and photographed with a high-speed camera. Conventional heating (oil bath or heating mantles) of the Pd(Pt)/CMCs and Pd(Pt)/ACs system led to significantly lower product yields. (C) 2012 Elsevier Inc. All rights reserved.
引用
收藏
页码:266 / 271
页数:6
相关论文
共 15 条
[1]  
Chen X, 2006, KONA, V24, P222
[2]  
Hajek M., 2006, Microwaves in Organic Synthesis, VSecond, P615, DOI DOI 10.1002/9783527619559.CH13
[3]   On the Generation of Hot-Spots by Microwave Electric and Magnetic Fields and Their Impact on a Microwave-Assisted Heterogeneous Reaction in the Presence of Metallic Pd Nanoparticles on an Activated Carbon Support [J].
Horikoshi, Satoshi ;
Osawa, Atsushi ;
Abe, Masahiko ;
Serpone, Nick .
JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (46) :23030-23035
[4]   A Novel Dewar-Like Reactor for Maintaining Constant Heat and Enhancing Product Yields during Microwave-Assisted Organic Syntheses [J].
Horikoshi, Satoshi ;
Osawa, Atsushi ;
Suttisawat, Yindee ;
Abe, Masahiko ;
Serpone, Nick .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (06) :1461-1464
[5]   Characterization of microwave effects on metal-oxide materials: Zinc oxide and titanium dioxide [J].
Horikoshi, Satoshi ;
Matsubara, Akihiro ;
Takayama, Sadatsugu ;
Sato, Motoyasu ;
Sakai, Futoshi ;
Kajitani, Masatsugu ;
Abe, Masahiko ;
Serpone, Nick .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2009, 91 (1-2) :362-367
[6]   Photochemistry with microwaves Catalysts and environmental applications [J].
Horikoshi, Satoshi ;
Serpone, Nick .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2009, 10 (02) :96-110
[7]   Organic materials for hydrogen storage applications: from physisorption on organic solids to chemisorption in organic molecules [J].
Makowski, Philippe ;
Thomas, Arne ;
Kuhn, Pierre ;
Goettmann, Frederic .
ENERGY & ENVIRONMENTAL SCIENCE, 2009, 2 (05) :480-490
[8]   Ball lightning plasma and plasma arc formation during the microwave heating of carbons [J].
Menendez, J. A. ;
Juarez-Perez, E. J. ;
Ruisanchez, E. ;
Bermudez, J. M. ;
Arenillas, A. .
CARBON, 2011, 49 (01) :346-349
[9]   Microwave heating processes involving carbon materials [J].
Menendez, J. A. ;
Arenillas, A. ;
Fidalgo, B. ;
Fernandez, Y. ;
Zubizarreta, L. ;
Calvo, E. G. ;
Bermudez, J. M. .
FUEL PROCESSING TECHNOLOGY, 2010, 91 (01) :1-8
[10]   Electromagnetic wave absorption properties of carbon microcoils/PMMA composite beads in W bands [J].
Motojima, S ;
Hoshiya, S ;
Hishikawa, Y .
CARBON, 2003, 41 (13) :2658-2660