Appel Reaction of Carboxylic Acids with Tribromoisocyanuric Acid/Triphenylphosphine: a Mild and Acid-Free Preparation of Esters and Amides

被引:9
作者
Sindra, Haryadylla da Cunha [1 ]
de Mattos, Marcio C. S. [1 ]
机构
[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, CP 68545, BR-21945970 Rio De Janeiro, RJ, Brazil
关键词
amides; esters; tribromoisocyanuric acid; acylation; triphenylphosphine; TRICHLOROISOCYANURIC ACID; REGIOSELECTIVE COIODINATION; TRIIODOISOCYANURIC ACID; FREE ESTERIFICATION; ALCOHOLS; REAGENT; TRIPHENYLPHOSPHINE; CONVERSION; CHLORIDES; BROMIDES;
D O I
10.5935/0103-5053.20160006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile and efficient method for esterification and amidation of carboxylic acids under neutral conditions has been developed. Esters and amides can be prepared by reacting a carboxylic acid (1 mmol) with tribromoisocyanuric acid (0.37 mmol) and triphenylphosphine (1 mmol) in dichloromethane at room temperature, followed by addition of an alcohol or an amine, respectively.
引用
收藏
页码:1129 / 1136
页数:8
相关论文
共 55 条
[11]   THE USE OF TRIBROMOISOCYANURIC ACID TO DISTINGUISH AMONG PRIMARY, SECONDARY AND TERTIARY ALCOHOLS [J].
Crespo, Livia T. C. ;
de Mattos, Marcio C. S. ;
Esteves, Pierre M. .
QUIMICA NOVA, 2013, 36 (02) :320-U153
[12]  
Ribeiro RD, 2012, J BRAZIL CHEM SOC, V23, P228, DOI 10.1590/S0103-50532012000200006
[13]   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
[14]   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
[15]   Tribromoisocyanuric Acid: A Green and Versatile Reagent [J].
de Almeida, Leonardo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
CURRENT GREEN CHEMISTRY, 2014, 1 (02) :94-107
[16]   Tribromoisocyanuric Acid in Trifluoroacetic Acid: An Efficient System for Smooth Brominating of Moderately Deactivated Arenes [J].
de Almeida, Leonardo S. ;
de Mattos, Marcio C. S. ;
Esteves, Pierre M. .
SYNLETT, 2013, 24 (05) :603-606
[17]   New Reagents and Synthetic Approaches to the Appel Reaction [J].
de Andrade, Vitor S. C. ;
de Mattos, Marcio C. S. .
CURRENT ORGANIC SYNTHESIS, 2015, 12 (03) :309-327
[18]   Tribromoisocyanuric Acid/Triphenylphosphine: a New System for Conversion of Alcohols into Alkyl Bromides [J].
de Andrade, Vitor S. C. ;
de Mattos, Marcio C. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2014, 25 (05) :975-979
[19]   Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis [J].
Fairfull-Smith, KE ;
Jenkins, ID ;
Loughlin, WA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) :1979-1986
[20]  
Giang L., 2007, NEW J CHEM, V31, P348