Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines

Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual u...

Descripción completa

Detalles Bibliográficos
Autores principales: Ishihara, Kazuaki, Lu, Yanhui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5975839/
https://www.ncbi.nlm.nih.gov/pubmed/29910884
http://dx.doi.org/10.1039/c5sc03761a
_version_ 1783327072623525888
author Ishihara, Kazuaki
Lu, Yanhui
author_facet Ishihara, Kazuaki
Lu, Yanhui
author_sort Ishihara, Kazuaki
collection PubMed
description Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate.
format Online
Article
Text
id pubmed-5975839
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-59758392018-06-15 Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines Ishihara, Kazuaki Lu, Yanhui Chem Sci Chemistry Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate. Royal Society of Chemistry 2016-02-01 2015-11-06 /pmc/articles/PMC5975839/ /pubmed/29910884 http://dx.doi.org/10.1039/c5sc03761a Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ishihara, Kazuaki
Lu, Yanhui
Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title_full Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title_fullStr Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title_full_unstemmed Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title_short Boronic acid–DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
title_sort boronic acid–dmapo cooperative catalysis for dehydrative condensation between carboxylic acids and amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5975839/
https://www.ncbi.nlm.nih.gov/pubmed/29910884
http://dx.doi.org/10.1039/c5sc03761a
work_keys_str_mv AT ishiharakazuaki boronicaciddmapocooperativecatalysisfordehydrativecondensationbetweencarboxylicacidsandamines
AT luyanhui boronicaciddmapocooperativecatalysisfordehydrativecondensationbetweencarboxylicacidsandamines

Ejemplares similares