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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...

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Autores principales: Ichitsuka, Tomohiro, Makino, Takashi, Ishizaka, Takayuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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