Sulfonic acid functionalized silica:: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide

被引:63
作者
Das, B [1 ]
Venkateswarlu, K [1 ]
Holla, H [1 ]
Krishnaiah, M [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
sulfonic acid functionalized silica; carbonyl compound; alpha-monobromination; NBS; heterogeneous recyclable catalyst;
D O I
10.1016/j.molcata.2006.03.011
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
Sulfonic acid functionalized silica has been found to be a highly efficient and versatile catalyst for alpha-monobromination of carbonyl compounds (cyclic and acyclic ketones, 1,3-diketones, beta-ketoesters, lactones, coumaranones and lactams) using N-bromosuccinimide under mild reaction conditions. The alpha-monobrominated products were obtained in very high yields and in short reaction times. The catalyst works under heterogeneous conditions and can be recyclable. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:107 / 111
页数:5
相关论文
共 21 条
[1]  
Bigelow L. A., 1943, ORG SYNTHESES COLL, V2,, P244
[2]   REGIOSPECIFIC SYNTHESIS OF UNSYMMETRICAL ALPHA-BROMOKETONES [J].
BOYD, RE ;
RASMUSSEN, CR ;
PRESS, JB .
SYNTHETIC COMMUNICATIONS, 1995, 25 (07) :1045-1051
[3]   Organic reactions catalyzed over solid acids [J].
Corma, A ;
Garcia, H .
CATALYSIS TODAY, 1997, 38 (03) :257-308
[4]   RATE CONSTANTS FOR HALOGEN ATOM TRANSFER FROM REPRESENTATIVE ALPHA-HALOCARBONYL COMPOUNDS TO PRIMARY ALKYL RADICALS [J].
CURRAN, DP ;
BOSCH, E ;
KAPLAN, J ;
NEWCOMB, M .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1826-1831
[5]   ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].
CURRAN, DP ;
CHANG, CT .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157
[6]   Studies on novel synthetic methodologies, part 59.: A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst [J].
Das, B ;
Venkateswarlu, K ;
Mahender, G ;
Mahender, L .
TETRAHEDRON LETTERS, 2005, 46 (17) :3041-3044
[7]   Combined alkyl and sulfonic acid functionalization of MCM-41-Type silica -: Part 2.: Esterification of glycerol with fatty acids [J].
Díaz, I ;
Márquez-Alvarez, C ;
Mohino, F ;
Pérez-Pariente, J ;
Sastre, E .
JOURNAL OF CATALYSIS, 2000, 193 (02) :295-302
[8]   BETA-METHYLENE-D,L-ASPARAGINE [J].
DOWD, P ;
KAUFMAN, C ;
KAUFMAN, P .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :882-885
[10]   REACTIONS WITH INDOLE-DERIVATIVES .55. AN ENANTIODIVERGENT ROUTE TO BOTH VINCAMINE ENANTIOMERS [J].
HAKAM, K ;
THIELMANN, M ;
THIELMANN, T ;
WINTERFELDT, E .
TETRAHEDRON, 1987, 43 (09) :2035-2044