Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles

A copper-catalyzed oxidative direct formation of amides from nonactivated carboxylic acids and azoles with dioxygen as an activating reagent is reported. The azole amides were produced in good to excellent yields with a broad substrate scope. The mechanistic studies reveal that oxygen plays an essen...

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Detalles Bibliográficos
Autores principales: Ding, Wen, Mai, Shaoyu, Song, Qiuling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660991/
https://www.ncbi.nlm.nih.gov/pubmed/26664637
http://dx.doi.org/10.3762/bjoc.11.233
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author Ding, Wen
Mai, Shaoyu
Song, Qiuling
author_facet Ding, Wen
Mai, Shaoyu
Song, Qiuling
author_sort Ding, Wen
collection PubMed
description A copper-catalyzed oxidative direct formation of amides from nonactivated carboxylic acids and azoles with dioxygen as an activating reagent is reported. The azole amides were produced in good to excellent yields with a broad substrate scope. The mechanistic studies reveal that oxygen plays an essential role in the success of the amidation reactions with copper peroxycarboxylate as the key intermediate. Transamidation occurs smoothly between azole amide and a variety of amines.
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spelling pubmed-46609912015-12-09 Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles Ding, Wen Mai, Shaoyu Song, Qiuling Beilstein J Org Chem Full Research Paper A copper-catalyzed oxidative direct formation of amides from nonactivated carboxylic acids and azoles with dioxygen as an activating reagent is reported. The azole amides were produced in good to excellent yields with a broad substrate scope. The mechanistic studies reveal that oxygen plays an essential role in the success of the amidation reactions with copper peroxycarboxylate as the key intermediate. Transamidation occurs smoothly between azole amide and a variety of amines. Beilstein-Institut 2015-11-11 /pmc/articles/PMC4660991/ /pubmed/26664637 http://dx.doi.org/10.3762/bjoc.11.233 Text en Copyright © 2015, Ding et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Ding, Wen
Mai, Shaoyu
Song, Qiuling
Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title_full Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title_fullStr Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title_full_unstemmed Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title_short Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
title_sort molecular-oxygen-promoted cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660991/
https://www.ncbi.nlm.nih.gov/pubmed/26664637
http://dx.doi.org/10.3762/bjoc.11.233
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AT songqiuling molecularoxygenpromotedcucatalyzedoxidativedirectamidationofnonactivatedcarboxylicacidswithazoles

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