Silica-supported policresulen as a solid acid catalyst for organic reactions

被引:25
作者
Zeng, Kexing [1 ]
Huang, Zhipeng [1 ]
Yang, Jie [1 ]
Gu, Yanlong [1 ,2 ]
机构
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Key Lab Large Format Battery Mat & Syst, Minist Educ, Wuhan 430074, Hubei, Peoples R China
[2] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
Acid catalysis; Solid acid; Policresulen; Covalent bond-free immobilization; oxa-Pictet-Spengler reaction; OXA-PICTET-SPENGLER; 1,3-DICARBONYL COMPOUNDS; BISMUTH TRIFLATE; ALCOHOLS; INDOLES; ALKENES; ISOCHROMANS; HYDROLYSIS; BIODIESEL; COUPLINGS;
D O I
10.1016/S1872-2067(15)60910-X
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new type of solid catalyst was prepared by coating a thin layer of policresulen, an inexpensive polymer prepared via condensation of 2-hydroxy-4-methylbenzenesulfonic acid and formaldehyde that has been used as commercially available drug, onto the surface of silica. The policresulen component is insoluble in many organic solvents and can be adsorbed on silica with the aid of hydrogen bonding. The obtained silica/policresulen composite showed remarkable catalytic activity for various organic reactions. In model reactions, the catalyst can be recycled several times without significant loss of activity. The salient features of using this acid catalyst in organic reactions include cost-effectiveness, simple and time-efficient preparation, and the convenience of controlling the acid loading on the solid. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1606 / 1613
页数:8
相关论文
共 61 条
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   A novel efficient method for the synthesis of substituted olefins; cross coupling of two different alcohols using NaHSO4/SiO2 [J].
Aoyama, Tadashi ;
Koda, Shuichi ;
Takeyoshi, Yuka ;
Ito, Tetsuhiro ;
Takido, Toshio ;
Kodomari, Mitsuo .
CHEMICAL COMMUNICATIONS, 2013, 49 (59) :6605-6607
[3]   Gold-catalysed direct couplings of indoles and pyrroles with 1,3-dicarbonyl compounds [J].
Arcadi, A ;
Alfonsi, M ;
Bianchi, G ;
D'Anniballe, G ;
Marinelli, F .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :331-338
[4]   BISMUTH TRIFLATE AS A SAFE AND READILY HANDLED SOURCE OF TRIFLIC ACID: APPLICATION TO THE OXA-PICTET-SPENGLER REACTION [J].
Bouguerne, Benaissa ;
Hoffmann, Pascal ;
Lherbet, Christian .
SYNTHETIC COMMUNICATIONS, 2010, 40 (06) :915-926
[5]   New trends in the design of supported catalysts on mesoporous silicas and their applications in fine chemicals [J].
Brunel, D ;
Blanc, AC ;
Galarneau, A ;
Fajula, F .
CATALYSIS TODAY, 2002, 73 (1-2) :139-152
[6]   Acid catalysts in industrial hydrocarbon chemistry [J].
Busca, Guido .
CHEMICAL REVIEWS, 2007, 107 (11) :5366-5410
[7]   Acid-catalyzed synthesis of mono- and dialkyl benzenes over zeolites:: Active sites, zeolite topology, and reaction mechanisms [J].
Cejka, J ;
Wichterlová, B .
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2002, 44 (03) :375-421
[8]   Lewis acids:: From conventional homogeneous to green homogeneous and heterogeneous catalysis [J].
Corma, A ;
García, H .
CHEMICAL REVIEWS, 2003, 103 (11) :4307-4365
[9]   Organic reactions catalyzed over solid acids [J].
Corma, A ;
Garcia, H .
CATALYSIS TODAY, 1997, 38 (03) :257-308
[10]   INORGANIC SOLID ACIDS AND THEIR USE IN ACID-CATALYZED HYDROCARBON REACTIONS [J].
CORMA, A .
CHEMICAL REVIEWS, 1995, 95 (03) :559-614