Tribromoisocyanuric Acid in Trifluoroacetic Acid: An Efficient System for Smooth Brominating of Moderately Deactivated Arenes

被引：25
作者：
de Almeida, Leonardo S. [1 ]
de Mattos, Marcio C. S. [1 ]
Esteves, Pierre M. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, BR-21945970 Rio De Janeiro, Brazil
来源：
SYNLETT | 2013年 / 24卷 / 05期
关键词：
arenes; electrophilic halogenation; bromination; deactivated aromatic compounds; tribromoisocyanuric acid; REGIOSELECTIVE COIODINATION; TRIIODOISOCYANURIC ACID; CONVENIENT REAGENT; ALKENES; IODINATION; COBROMINATION; CHLORINATION;
D O I：
10.1055/s-0032-1317795
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H2SO4.
引用
收藏
页码：603 / 606
页数：4
相关论文
共 28 条
[1]   Bromination of deactivated aromatic compounds [J].
Andrievsky, A. M. ;
Gorelik, M. V. .
RUSSIAN CHEMICAL REVIEWS, 2011, 80 (05) :421-428
[2]   QUINAZOLINES AND 1,4-BENZODIAZEPINES .82. 5-PYRIMIDYLBENZODIAZEPINES AND 5-PYRAZINYLBENZODIAZEPINES [J].
ARCHER, GA ;
KALISH, RI ;
NING, RY ;
SLUBOSKI, BC ;
STEMPEL, A ;
STEPPE, TV ;
STERNBACH, LH .
JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (10) :1312-1317
[3]   The progressive bromination of toluene. [J].
Cohen, JB ;
Dutt, PK .
JOURNAL OF THE CHEMICAL SOCIETY, 1914, 105 :501-521
[4]   Halofluorination of Alkenes Using Trihaloisocyanuric Acids and HF•Pyridine [J].
Crespo, Livia T. C. ;
Ribeiro, Rodrigo da S. ;
de Mattos, Marcio C. S. ;
Esteves, Pierre M. .
SYNTHESIS-STUTTGART, 2010, (14) :2379-2382
[5]   Tetraalkylphosphonium Trihalides. Room Temperature Ionic Liquids As Halogenation Reagents [J].
Cristiano, Rodrigo ;
Ma, Kefeng ;
Pottanat, George ;
Weiss, Richard G. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :9027-9033
[6]   Superelectrophilic Iodination of Deactivated Arenes with Triiodoisocyanuric Acid [J].
da Ribeiro, Rodrigo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
SYNTHESIS-STUTTGART, 2011, (05) :739-744
[7]  
Ribeiro RD, 2012, J BRAZIL CHEM SOC, V23, P228, DOI 10.1590/S0103-50532012000200006
[8]   Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions [J].
de Almeida, Leonardo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
SYNLETT, 2007, (11) :1687-1690
[9]   Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes [J].
de Almeida, Leonardo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
SYNLETT, 2006, (10) :1515-1518
[10]   Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid-an experimental and DFT study [J].
de Almeida, Leonardo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
TETRAHEDRON LETTERS, 2009, 50 (25) :3001-3004
123