Decarboxylative bromination of cinnamic acids by 2-iodoxybenzoic acid with tetrabutylammonium bromide

被引:5
作者
Han, Jianlei [1 ]
Wei, Yuping [1 ]
机构
[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
bromostyrenes; cinnamic acids; 2-iodoxybenzoic acid; tetrabutylammonium bromide; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; MICROWAVE-INDUCED REACTION; CATALYTIC HUNSDIECKER REACTION; STEREOSELECTIVE-SYNTHESIS; ALPHA-IMINONITRILES; TERMINAL ALKYNES; EFFICIENT METHOD; VINYL-BROMIDES; HALIDES; SYSTEM;
D O I
10.3184/174751912X13324352705972
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The decarboxylative bromination of cinnamic acids using the hypervalent iodine reagent 2-iodoxybenzoic acid with tetrabutylammoniunn bromide is described, providing good to excellent yields of bromostyrenes. Bromostyrenes are useful coupling components in a wide range of transition metal-catalysed coupling reactions.
引用
收藏
页码:247 / 248
页数:2
相关论文
共 30 条
[1]   o-Iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles [J].
Bhalerao, Dinesh S. ;
Mahajan, Ulhas S. ;
Chaudhari, Kiran H. ;
Akamanchi, Krishnacharya G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :662-665
[2]   Convenient One-Pot Synthesis of (E)-β-Aryl Vinyl Halides from Benzyl Bromides and Dihalomethanes [J].
Bull, James A. ;
Mousseau, James J. ;
Charette, Andre B. .
ORGANIC LETTERS, 2008, 10 (23) :5485-5488
[3]   Hunsdiecker-type bromodecarboxylation of carboxylic acids with iodosobenzene diacetate-bromine [J].
Camps, P ;
Lukach, AE ;
Pujol, X ;
Vázquez, S .
TETRAHEDRON, 2000, 56 (17) :2703-2707
[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]   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
[6]   2-Iodoxybenzoic Acid-A Simple Oxidant with a Dazzling Array of Potential Applications [J].
Duschek, Alexander ;
Kirsch, Stefan F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) :1524-1552
[7]   One-pot three-component synthesis of α-iminonitriles by IBX/TBAB-Mediated oxidative Strecker reaction [J].
Fontaine, Patrice ;
Chiaroni, Angele ;
Masson, Geraldine ;
Zhu, Jieping .
ORGANIC LETTERS, 2008, 10 (08) :1509-1512
[8]   Synthesis of Pyrroles by Consecutive Multicomponent Reaction/[4+1] Cycloaddition of α-Iminonitriles with Isocyanides [J].
Fontaine, Patrice ;
Masson, Geraldine ;
Zhu, Jieping .
ORGANIC LETTERS, 2009, 11 (07) :1555-1558
[9]   Novel System for Decarboxylative Bromination of α,β-Unsaturated Carboxylic Acids with Diacetoxyiodobenzene [J].
Fursule, Ravindra Abhykumar ;
Patil, Pravin Onkar ;
Shewale, Bharti Devaji ;
Kosalge, Satish Bhaskar ;
Deshmukh, Prashant Krishnarao ;
Patil, Dilip Ashok .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (11) :1243-1245
[10]   α-Selective Ni-Catalyzed Hydroalumination of Aryl- and Alkyl-Substituted Terminal Alkynes: Practical Syntheses of Internal Vinyl Aluminums, Halides, or Boronates [J].
Gao, Fang ;
Hoveyda, Amir H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) :10961-10963