An efficient microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 as catalysts in solvent-free condition

被引:23
作者
Chang, Wonghil [1 ,2 ]
Chae, GeumHee [3 ]
Jang, So Ra [3 ]
Shin, Jihye [1 ,2 ]
Ahn, Byoung Joon [3 ]
机构
[1] Jeonju Univ, Dept Basic Med Sci, Jeonju 560759, South Korea
[2] Jeonju Univ, EM R&D Ctr, Jeonju 560759, South Korea
[3] Chonbuk Natl Univ, Inst Sci Educ, Inst Fus Sci, Dept Chem Educ, Jeonju 561756, South Korea
关键词
Microwave; Suzuki reaction; Pd/MCM-41; Pd/SBA-15; Solvent-free; CROSS-COUPLING REACTIONS; NONCONVENTIONAL METHODOLOGIES; HETEROGENEOUS SUZUKI; ARYL HALIDES; PALLADIUM; CARBON;
D O I
10.1016/j.jiec.2011.11.043
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium catalysts, Pd/MCM-41 and Pd/SBA-15 were prepared by impregnation of an aqueous solution of [Pd(NH3)(4)]Cl-2 on MCM-41 and SBA-15. Palladium contents of Pd/MCM-41 and Pd/SBA-15 are 8.4% and 8.7%, respectively. It has been shown that these catalysts are very suitable to microwave-assisted Suzuki reactions under solvent-free condition. It is also found that the base additives for this reaction are K2CO3, Cs2CO3 or CsF. Thus, phenylboronic acid and phenyl iodide with Pd/MCM-41 produce biphenyl by microwave irradiation for 10 min in 97.4% yield. Phenyl bromide, instead of phenyl iodide, also proceeds the reaction with phenylboronic acid using Pd/MCM-41 or Pd/SBA-15 yielding biphenyl by microwave irradiation for 10 min in excellent yield. Whereas the reaction of phenyl chloride with phenylboronic acid gives poor yield in same condition. Various aryl iodides and aryl bromides are tested. In this paper our recent results of microwave-assisted Suzuki reaction using Pd/MCM-41 and Pd/SBA-15 under solvent-free condition are described. (C) 2011 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:581 / 585
页数:5
相关论文
共 26 条
[1]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
TETRAHEDRON, 2005, 61 (50) :11771-11835
[2]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].
Alonso, Francisco ;
Beletskaya, Irina P. ;
Yus, Miguel .
TETRAHEDRON, 2008, 64 (14) :3047-3101
[3]  
Anastas P., 1998, GREEN CHEM THEORY PR
[4]  
[Anonymous], 2000, Green Chemistry, Challenging Perspectives
[5]   Heterogeneous suzuki reactions catalyzed by Pd(0)-Y zeolite [J].
Artok, L ;
Bulut, H .
TETRAHEDRON LETTERS, 2004, 45 (20) :3881-3884
[6]  
Augustine R.L., 1996, HETEROGENEOUS CATALY
[7]   Suzuki cross-coupling reactions of aryl halides with arylboronic acids catalysed by Pd(II)-NaY zeolite [J].
Bulut, H ;
Artok, L ;
Yilmaz, S .
TETRAHEDRON LETTERS, 2003, 44 (02) :289-291
[8]  
Cepanec I., 2004, Synthesis of Biaryls
[9]   A simple and efficient Suzuki reaction catalyzed by palladium-modified nanopore silica under solvent-free conditions [J].
Chang, Wonghil ;
Shin, Jihye ;
Oh, Yunghee ;
Ahn, Byoung Joon .
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2008, 14 (04) :423-428
[10]   Selected patented cross-coupling reaction technologies [J].
Corbet, Jean-Pierre ;
Mignani, Gerard .
CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710