Chemoselective N-acylation of indoles using thioesters as acyl source

The selective acylation of indoles often requires sensitive and reactive acyl chloride derivatives. Here, we report a mild, efficient, functional group tolerant, and highly chemoselective N-acylation of indoles using thioesters as a stable acyl source. A series of indoleamides have been obtained wit...

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Detalles Bibliográficos
Autores principales: Du, Tianri, Wei, Xiangmu, Xu, Honghong, Zhang, Xin, Fang, Ruiru, Yuan, Zheng, Liang, Zhi, Li, Yahui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767559/
https://www.ncbi.nlm.nih.gov/pubmed/35096177
http://dx.doi.org/10.3762/bjoc.18.9
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author Du, Tianri
Wei, Xiangmu
Xu, Honghong
Zhang, Xin
Fang, Ruiru
Yuan, Zheng
Liang, Zhi
Li, Yahui
author_facet Du, Tianri
Wei, Xiangmu
Xu, Honghong
Zhang, Xin
Fang, Ruiru
Yuan, Zheng
Liang, Zhi
Li, Yahui
author_sort Du, Tianri
collection PubMed
description The selective acylation of indoles often requires sensitive and reactive acyl chloride derivatives. Here, we report a mild, efficient, functional group tolerant, and highly chemoselective N-acylation of indoles using thioesters as a stable acyl source. A series of indoleamides have been obtained with moderate to good yields. In addition, heterocycles, such as carbazole, can also be used as nucleophiles in this reaction.
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spelling pubmed-87675592022-01-27 Chemoselective N-acylation of indoles using thioesters as acyl source Du, Tianri Wei, Xiangmu Xu, Honghong Zhang, Xin Fang, Ruiru Yuan, Zheng Liang, Zhi Li, Yahui Beilstein J Org Chem Full Research Paper The selective acylation of indoles often requires sensitive and reactive acyl chloride derivatives. Here, we report a mild, efficient, functional group tolerant, and highly chemoselective N-acylation of indoles using thioesters as a stable acyl source. A series of indoleamides have been obtained with moderate to good yields. In addition, heterocycles, such as carbazole, can also be used as nucleophiles in this reaction. Beilstein-Institut 2022-01-10 /pmc/articles/PMC8767559/ /pubmed/35096177 http://dx.doi.org/10.3762/bjoc.18.9 Text en Copyright © 2022, Du et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Du, Tianri
Wei, Xiangmu
Xu, Honghong
Zhang, Xin
Fang, Ruiru
Yuan, Zheng
Liang, Zhi
Li, Yahui
Chemoselective N-acylation of indoles using thioesters as acyl source
title Chemoselective N-acylation of indoles using thioesters as acyl source
title_full Chemoselective N-acylation of indoles using thioesters as acyl source
title_fullStr Chemoselective N-acylation of indoles using thioesters as acyl source
title_full_unstemmed Chemoselective N-acylation of indoles using thioesters as acyl source
title_short Chemoselective N-acylation of indoles using thioesters as acyl source
title_sort chemoselective n-acylation of indoles using thioesters as acyl source
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767559/
https://www.ncbi.nlm.nih.gov/pubmed/35096177
http://dx.doi.org/10.3762/bjoc.18.9
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