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Atom-Economical Synthesis of N-Arylamides Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts
[Image: see text] Existing methods for the catalytic synthesis of N-arylamides are limited by a narrow substrate scope, high catalyst costs, and complicated purification processes of products. To overcome these limitations, this study developed an ecofriendly method for the synthesis of N-arylamides...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10688214/ https://www.ncbi.nlm.nih.gov/pubmed/38046317 http://dx.doi.org/10.1021/acsomega.3c06080 |
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author | Ichitsuka, Tomohiro Makino, Takashi Ishizaka, Takayuki |
author_facet | Ichitsuka, Tomohiro Makino, Takashi Ishizaka, Takayuki |
author_sort | Ichitsuka, Tomohiro |
collection | PubMed |
description | [Image: see text] Existing methods for the catalytic synthesis of N-arylamides are limited by a narrow substrate scope, high catalyst costs, and complicated purification processes of products. To overcome these limitations, this study developed an ecofriendly method for the synthesis of N-arylamides using isopropenyl esters. Isopropenyl esters activated using heterogeneous acid catalysts reacted smoothly even with less reactive arylamines to afford N-arylamides in high yields. This method exhibits a wide substrate scope and is applicable for the synthesis of various N-arylamides (33 examples, 46–99% yield). The developed method enabled the obtainment of high-purity products with a facile workup procedure and showed excellent process mass intensity values due to the reduction of chemical waste. |
format | Online Article Text |
id | pubmed-10688214 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-106882142023-12-01 Atom-Economical Synthesis of N-Arylamides Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts Ichitsuka, Tomohiro Makino, Takashi Ishizaka, Takayuki ACS Omega [Image: see text] Existing methods for the catalytic synthesis of N-arylamides are limited by a narrow substrate scope, high catalyst costs, and complicated purification processes of products. To overcome these limitations, this study developed an ecofriendly method for the synthesis of N-arylamides using isopropenyl esters. Isopropenyl esters activated using heterogeneous acid catalysts reacted smoothly even with less reactive arylamines to afford N-arylamides in high yields. This method exhibits a wide substrate scope and is applicable for the synthesis of various N-arylamides (33 examples, 46–99% yield). The developed method enabled the obtainment of high-purity products with a facile workup procedure and showed excellent process mass intensity values due to the reduction of chemical waste. American Chemical Society 2023-11-13 /pmc/articles/PMC10688214/ /pubmed/38046317 http://dx.doi.org/10.1021/acsomega.3c06080 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Ichitsuka, Tomohiro Makino, Takashi Ishizaka, Takayuki Atom-Economical Synthesis of N-Arylamides Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title | Atom-Economical Synthesis of N-Arylamides
Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title_full | Atom-Economical Synthesis of N-Arylamides
Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title_fullStr | Atom-Economical Synthesis of N-Arylamides
Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title_full_unstemmed | Atom-Economical Synthesis of N-Arylamides
Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title_short | Atom-Economical Synthesis of N-Arylamides
Utilizing Isopropenyl Esters with Heterogeneous Acid Catalysts |
title_sort | atom-economical synthesis of n-arylamides
utilizing isopropenyl esters with heterogeneous acid catalysts |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10688214/ https://www.ncbi.nlm.nih.gov/pubmed/38046317 http://dx.doi.org/10.1021/acsomega.3c06080 |
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