Comparative behavior of silica-embedded tert-butyldimethylsilyltrifluoro-methanesulfonate and lanthanum triflate catalysts

被引:11
作者
Pârvulescu, AN
Gagea, BC
Pârvulescu, V
Pârvulescu, VI
Poncelet, G
Grange, P
机构
[1] Univ Bucharest, Dept Chem Technol & Catalysis, Fac Chem, Bucharest 70346, Romania
[2] Romanian Acad Sci, Inst Phys Chem, Bucharest, Romania
[3] Univ Catholique Louvain, Unite Catalyse & Chim Mat Divises, B-1348 Louvain, Belgium
关键词
tert-butyidimethylsilyltrifluoro-methanesulfonate; lanthanum triflate; 3-methylbenzaldehyde; hexadecyltrimethylammonium bromide; silica; methyl ester of 1-cyclopentenylacetic acid;
D O I
10.1016/S0920-5861(01)00510-7
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of hybrid catalysts containing tert-butyldimethylsilyltrifluoro-methanesulfonate (BDMST) or lanthanum triflate (LaT), hex adecyltrimethylammonium bromide and silica were obtained by sol-gel immobilization. The catalysts were characterized by nitrogen adsorption-desorption isotherms at 77 K, TG-DTA, H-1, C-13, and Si-29 solid state MAS-NMR, XRD, TEM, scanning electron microscopy (SEM), XPS and, FT-IR after adsorption of NH3. The catalytic tests were carried out in the reaction of the methyl ester of 1-cyclopentenylacetic acid in various solvents. The results revealed a completely different behavior of the hybrid catalysts compared with catalysts without surfactant or with free tert-butyldimethylsilyltrifluoro-methanesulfonate, or lanthanum triflate, or triflic acid, indicating a behavior for a typical heterogeneous catalyst. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:177 / 185
页数:9
相关论文
共 16 条
[1]   Scandium trifluoromethanesulfonate, a novel catalyst for the addition of allyltrimethylsilane to aldehydes. [J].
Aggarwal, VK ;
Vennall, GP .
TETRAHEDRON LETTERS, 1996, 37 (21) :3745-3746
[2]   Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid [J].
Barrett, AGM ;
Braddock, DC .
CHEMICAL COMMUNICATIONS, 1997, (04) :351-352
[3]  
CHEN QY, 1988, SYNTHESIS-STUTTGART, P866
[4]  
CLERICI MG, 1995, Patent No. 638363
[5]  
DRYSDALE NE, 1994, Patent No. 9502625
[6]  
EFFENBERGER F, 1982, CHEM BER-RECL, V115, P1089, DOI 10.1002/cber.19821150325
[7]   Novel and facile selective reduction of carboxylic acid with a samarium diiodide-lanthanide triflate-methanol-base system [J].
Kamochi, Y ;
Kudo, T .
TETRAHEDRON LETTERS, 2000, 41 (03) :341-344
[8]   ASYMMETRIC DIELS-ALDER REACTIONS CATALYZED BY CHIRAL LANTHANIDE(III) TRIFLUOROMETHANESULFONATES - UNIQUE STRUCTURE OF THE TRIFLATE AND STEREOSELECTIVE SYNTHESIS OF BOTH ENANTIOMERS USING A SINGLE CHIRAL SOURCE AND A CHOICE OF ACHIRAL LIGANDS [J].
KOBAYASHI, S ;
ISHITANI, H ;
HACHIYA, I ;
ARAKI, M .
TETRAHEDRON, 1994, 50 (40) :11623-11636
[9]   Aldol reactions on solid phase. Sc(OTf)(3)-catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol,beta-hydroxy carboxylic acid, and beta-hydroxy aldehyde libraries [J].
Kobayashi, S ;
Hachiya, I ;
Yasuda, M .
TETRAHEDRON LETTERS, 1996, 37 (31) :5569-5572
[10]  
MURATA S, 1980, TETRAHEDRON LETT, V21, P1357