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

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2016年 / 27卷 / 06期

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

页码：1129 / 1136

页数：8

共 55 条

[31]

Kosal A. D., 2013, GREEN CHEM, V15, P1255

[32] Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides [J].

Kosal, Andrew D. ;

Wilson, Erin E. ;

Ashfeld, Brandon L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) :12036-12040

[33] Substrate-Selective Dehydrocondensation at the Interface of Micelles and Emulsions of Common Surfactants [J].

Kunishima, Munetaka ;

Kikuchi, Kanako ;

Kawai, Yukio ;

Hioki, Kazuhito .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) :2080-2083

[34]

Larock R.C., 1989, Comprehensive Organic Transformations: A Guide to Functional Group Preparations

[35] PREPARATION OF ACYL HALIDES UNDER VERY MILD CONDITIONS [J].

LEE, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3440-&

[36] Heterometal Clusters Ln2Na8(OCH2CH2NMe2)12(OH)2 as Homogeneous Catalysts for the Tishchenko Reaction [J].

Li Lan ;

Sheng Hongting ;

Xu Fan ;

Shen Qi .

CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (06) :1127-1131

[37] Action of thionyl chloride on organic acids [J].

McMaster, L ;

Ahmann, FF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1928, 50 :145-149

[38]

Mendonça GF, 2013, CURR ORG SYNTH, V10, P820

[39] Hexabromoacetone as tribromoacetylating agent of alcohols and amines and as mediator in the conversion of carboxylic acids into amides in the presence of triphenylphosphine [J].

Menezes, Fabricio G. ;

Kolling, Rosane ;

Bortoluzzi, Adailton J. ;

Gallardo, Hugo ;

Zucco, Cesar .

TETRAHEDRON LETTERS, 2009, 50 (21) :2559-2561

[40]

Negwer M., 2001, Organic-Chemical Drugs and Their Synonyms, V8th

← 1 2 3 4 5 6 →