Mild and efficient method for decarboxylative bromination of α,β-unsaturated carboxylic acids with Dess-Martin periodinane

被引:35
作者
Telvekar, VN [1 ]
Arote, ND [1 ]
Herlekar, OP [1 ]
机构
[1] Univ Bombay, Inst Chem Technol, Dept Pharmaceut Sci & Technol, Bombay 400019, Maharashtra, India
关键词
Dess-Martin periodinane; tetraethylammonium; bromide; decaboxylation; bromoalkenes;
D O I
10.1055/s-2005-917077
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and mild method for decarboxylative broinination of alpha,beta-unsaturated carboxylic acids has been developed using Dess-Martin Periodinane (DMP) in combination with tetraethylammonium bromide (TEA B) at room temperature. High yields of the corresponding bromoalkenes were obtained.
引用
收藏
页码:2495 / 2497
页数:3
相关论文
共 21 条
[1]   PHOTOCHEMICAL TRANSFORMATIONS .17. IMPROVED METHODS FOR DECARBOXYLATION OF ACIDS [J].
BARTON, DHR ;
FARO, HP ;
SEREBRYAKOV, EP ;
WOOLSEY, NF .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (APR) :2438-+
[2]   Deoximation using Dess-Martin periodinane: Regeneration of ketones from ketoximes [J].
Chaudhari, SS ;
Akamanchi, KG .
TETRAHEDRON LETTERS, 1998, 39 (20) :3209-3212
[3]  
Chaudhari SS, 1999, SYNTHESIS-STUTTGART, P760
[4]   Manganese(II) catalysed Hunsdiecker reaction: A facile entry to alpha-(dibromomethyl) benzenemethanol [J].
Chowdhury, S ;
Roy, S .
TETRAHEDRON LETTERS, 1996, 37 (15) :2623-2624
[5]   A CONVENIENT SYNTHESIS OF ALKYL HALIDES FROM CARBOXYLIC ACIDS [J].
CRISTOL, SJ ;
FIRTH, WC .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (01) :280-&
[6]   Catalytic hunsdiecker reaction of α,β-unsaturated carboxylic acids:: How efficient is the catalyst? [J].
Das, JP ;
Roy, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (22) :7861-7864
[7]   OXIDATIVE HALO-DECARBOXYLATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS [J].
GRAVEN, A ;
JORGENSEN, KA ;
DAHL, S ;
STANCZAK, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3543-3546
[8]   Halodecarboxylation of α,β-acetylenic and α,β-ethylenic acids [J].
Homsi, F ;
Rousseau, G .
TETRAHEDRON LETTERS, 1999, 40 (08) :1495-1498
[9]   4-endo-trig cyclization processes using bis(collidine)bromine(I)hexafluorophosphate as reagent:: Preparation of 2-oxetanones, 2-azetidinones, and oxetanes [J].
Homsi, F ;
Rousseau, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :81-85
[10]   Concerning the breakdown aliphatic acid salts by bromine. [J].
Hunsdiecker, H ;
Hunsdiecker, C .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1942, 75 :291-297