Cargando…

Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions

N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterificatio...

Descripción completa

Detalles Bibliográficos
Autores principales: Čebular, Klara, Božić, Bojan Đ., Stavber, Stojan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225170/
https://www.ncbi.nlm.nih.gov/pubmed/30200547
http://dx.doi.org/10.3390/molecules23092235
_version_ 1783369713779212288
author Čebular, Klara
Božić, Bojan Đ.
Stavber, Stojan
author_facet Čebular, Klara
Božić, Bojan Đ.
Stavber, Stojan
author_sort Čebular, Klara
collection PubMed
description N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.
format Online
Article
Text
id pubmed-6225170
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62251702018-11-13 Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions Čebular, Klara Božić, Bojan Đ. Stavber, Stojan Molecules Article N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed. MDPI 2018-09-02 /pmc/articles/PMC6225170/ /pubmed/30200547 http://dx.doi.org/10.3390/molecules23092235 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Čebular, Klara
Božić, Bojan Đ.
Stavber, Stojan
Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title_full Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title_fullStr Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title_full_unstemmed Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title_short Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
title_sort esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6225170/
https://www.ncbi.nlm.nih.gov/pubmed/30200547
http://dx.doi.org/10.3390/molecules23092235
work_keys_str_mv AT cebularklara esterificationofarylalkylacidscatalysedbynbromosuccinimideundermildreactionconditions
AT bozicbojanđ esterificationofarylalkylacidscatalysedbynbromosuccinimideundermildreactionconditions
AT stavberstojan esterificationofarylalkylacidscatalysedbynbromosuccinimideundermildreactionconditions