TMS-OTf-catalyzed α-bromination of carbonyl compounds by N-bromosuccinimide

被引:44
作者
Guha, SK [1 ]
Wu, B [1 ]
Kim, BS [1 ]
Baik, W [1 ]
Koo, S [1 ]
机构
[1] Myong Ji Univ, Dept Chem, Yongin 449728, Kyunggi, South Korea
关键词
D O I
10.1016/j.tetlet.2005.11.023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various carbonyl compounds undergo alpha-bromination reaction under a mild and practical condition utilizing N-bromosuccinimide (NBS), catalyzed by trimethylsilyl trifluoromethanesulfonate ((TMSOTf)-O-.). This method is also effective for the side-chain bromination of heteroaromatic carbonyl compounds without the ring brominations. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:291 / 293
页数:3
相关论文
共 23 条
[1]   BROMINATING PROPERTIES OF TETRAMETHYLAMMONIUM TRIBROMIDE [J].
AVRAMOFF, M ;
SCHACHTER, O ;
WEISS, J .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (11) :3256-&
[2]   N-Methylpyrrolidin-2-one hydrotribromide (MPHT) a mild reagent for selective bromination of carbonyl compounds:: synthesis of substituted 2-bromo-1-naphtols [J].
Bekaert, A ;
Provot, O ;
Rasolojaona, O ;
Alami, M ;
Brion, JD .
TETRAHEDRON LETTERS, 2005, 46 (24) :4187-4191
[3]  
Bigelow L. A., 1943, ORG SYNTHESES COLL, V2,, P244
[4]  
BLANCO L, 1976, SYNTHESIS-STUTTGART, P194
[5]   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
[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]  
De Kimpe N., 1988, ALPHA HALOKETONES AL
[9]  
Hambly G. F., 1986, TETRAHEDRON LETT, V27, P2563
[10]   REACTIONS OF HYDROCARBON CHAIN OF FATTY ACIDS [J].
HARWOOD, HJ .
CHEMICAL REVIEWS, 1962, 62 (02) :99-+