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Catalytic N-methyl amidation of carboxylic acids under cooperative conditions

Amide is a fundamental group that is present in molecular structures of all domains of organic chemistry and the construction of this motif with high atom economy is the focus of the current research. Specifically, N-methyl amides are valuable building blocks in natural products and pharmaceutical s...

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Autores principales: Yingxian, Li, Wei, Chen, Linchun, Zhao, Ji-Quan, Zhang, Yonglong, Zhao, Chun, Li, Bing, Guo, Lei, Tang, Yuan-Yong, Yang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9284536/
https://www.ncbi.nlm.nih.gov/pubmed/35919177
http://dx.doi.org/10.1039/d2ra03255d
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author Yingxian, Li
Wei, Chen
Linchun, Zhao
Ji-Quan, Zhang
Yonglong, Zhao
Chun, Li
Bing, Guo
Lei, Tang
Yuan-Yong, Yang
author_facet Yingxian, Li
Wei, Chen
Linchun, Zhao
Ji-Quan, Zhang
Yonglong, Zhao
Chun, Li
Bing, Guo
Lei, Tang
Yuan-Yong, Yang
author_sort Yingxian, Li
collection PubMed
description Amide is a fundamental group that is present in molecular structures of all domains of organic chemistry and the construction of this motif with high atom economy is the focus of the current research. Specifically, N-methyl amides are valuable building blocks in natural products and pharmaceutical science. Due to the volatile nature of methyl amine, the generation of N-methyl amides using simple acids with high atom economy is rare. Herein, we disclose an atom economic protocol to prepare this valuable motif under DABCO/Fe(3)O(4) cooperative catalysis. This protocol is operationally simple and compatible with a range of aliphatic and (hetero)aromatic acids with very good yields (60–99%). Moreover, the Fe(3)O(4) can be easily recovered and high efficiency is maintained for up to ten cycles.
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spelling pubmed-92845362022-08-01 Catalytic N-methyl amidation of carboxylic acids under cooperative conditions Yingxian, Li Wei, Chen Linchun, Zhao Ji-Quan, Zhang Yonglong, Zhao Chun, Li Bing, Guo Lei, Tang Yuan-Yong, Yang RSC Adv Chemistry Amide is a fundamental group that is present in molecular structures of all domains of organic chemistry and the construction of this motif with high atom economy is the focus of the current research. Specifically, N-methyl amides are valuable building blocks in natural products and pharmaceutical science. Due to the volatile nature of methyl amine, the generation of N-methyl amides using simple acids with high atom economy is rare. Herein, we disclose an atom economic protocol to prepare this valuable motif under DABCO/Fe(3)O(4) cooperative catalysis. This protocol is operationally simple and compatible with a range of aliphatic and (hetero)aromatic acids with very good yields (60–99%). Moreover, the Fe(3)O(4) can be easily recovered and high efficiency is maintained for up to ten cycles. The Royal Society of Chemistry 2022-07-15 /pmc/articles/PMC9284536/ /pubmed/35919177 http://dx.doi.org/10.1039/d2ra03255d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yingxian, Li
Wei, Chen
Linchun, Zhao
Ji-Quan, Zhang
Yonglong, Zhao
Chun, Li
Bing, Guo
Lei, Tang
Yuan-Yong, Yang
Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title_full Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title_fullStr Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title_full_unstemmed Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title_short Catalytic N-methyl amidation of carboxylic acids under cooperative conditions
title_sort catalytic n-methyl amidation of carboxylic acids under cooperative conditions
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9284536/
https://www.ncbi.nlm.nih.gov/pubmed/35919177
http://dx.doi.org/10.1039/d2ra03255d
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