Direct alkylation of aromatics using alcohols in the presence of NaHSO4/SiO2

被引:53
作者
Sato, Yuta [1 ]
Aoyama, Tadashi [1 ]
Takido, Toshio [1 ]
Kodomari, Mitsuo [2 ]
机构
[1] Nihon Univ, Coll Sci & Technol, Dept Mat & Appl Chem, Chiyoda Ku, Tokyo 1018308, Japan
[2] Shibaura Inst Technol, Dept Biosci & Engn, Minuma Ku, Saitama 3378570, Japan
关键词
Alkylation; Aromatics; Supported reagent; Alcohol; FRIEDEL-CRAFTS ARYLATION; BENZYL ALCOHOLS; ARENES; EFFICIENT; CATALYST; ACTIVATION;
D O I
10.1016/j.tet.2012.06.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could be recycled eight times without activity loss. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7077 / 7081
页数:5
相关论文
共 22 条
[1]   Direct Carbon-Carbon Bond Formation from Alcohols and Active Methylenes using NaHSO4/SiO2 [J].
Aoyama, Tadashi ;
Miyota, Saki ;
Takido, Toshio ;
Kodomari, Mitsuo .
SYNLETT, 2011, (20) :2971-2976
[3]   Silicagel supported sodium hydrogensulfate as a heterogenous catalyst for high yield synthesis of 3,4-dihydropyrimidin-2 (1H)-ones [J].
Chari, MA ;
Syamasundar, K .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 221 (1-2) :137-139
[4]   A novel method for sulfonation of aromatic rings with silica sulfuric acid [J].
Hajipour, AR ;
Mirjalili, BBF ;
Zarei, A ;
Khazdooz, L ;
Ruoho, AE .
TETRAHEDRON LETTERS, 2004, 45 (35) :6607-6609
[5]   An efficient and general iron-catalyzed arylation of benzyl alcohols and benzyl carboxylates [J].
Iovel, I ;
Mertins, K ;
Kischel, J ;
Zapf, A ;
Beller, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3913-3917
[6]   Recyclable graphite oxide catalyzed Friedel-Crafts addition of indoles to α,β-unsaturated ketones [J].
Kumar, A. Vijay ;
Rao, K. Rama .
TETRAHEDRON LETTERS, 2011, 52 (40) :5188-5191
[7]   Bronsted-acid-catalyzed coupling of electron-rich arenes with substituted allylic and secondary benzylic alcohols [J].
Le Bras, Jean ;
Muzart, Jacques .
TETRAHEDRON, 2007, 63 (33) :7942-7948
[8]   An Efficient and General Iron-Catalyzed C-C Bond Activation with 1,3-Dicarbonyl Units as a Leaving Groups [J].
Li, Huanrong ;
Li, Wenjuan ;
Liu, Weiping ;
He, Zhiheng ;
Li, Zhiping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (13) :2975-2978
[9]   Organocatalyzed Friedel-Crafts arylation of benzylic alcohols [J].
McCubbin, J. Adam ;
Krokhin, Oleg V. .
TETRAHEDRON LETTERS, 2010, 51 (18) :2447-2449
[10]   Gold-catallyzed benzylation of arenes and heteroarenes [J].
Mertins, K ;
Lovel, I ;
Kischel, J ;
Zapf, A ;
Beller, M .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :691-695