Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions

In a ball mill, FeBr(3)‐catalyzed intramolecular amidations lead to 3,4‐dihydro‐2(1H)‐quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4‐substituted aryl and β‐substituted di...

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Autores principales: Shi, Peng, Tu, Yongliang, Kong, Deshen, Wu, Peng, Ma, Ding, Bolm, Carsten
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401578/
https://www.ncbi.nlm.nih.gov/pubmed/35511087
http://dx.doi.org/10.1002/anie.202204874
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author Shi, Peng
Tu, Yongliang
Kong, Deshen
Wu, Peng
Ma, Ding
Bolm, Carsten
author_facet Shi, Peng
Tu, Yongliang
Kong, Deshen
Wu, Peng
Ma, Ding
Bolm, Carsten
author_sort Shi, Peng
collection PubMed
description In a ball mill, FeBr(3)‐catalyzed intramolecular amidations lead to 3,4‐dihydro‐2(1H)‐quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4‐substituted aryl and β‐substituted dioxazolones provide products with high selectivity. Mechanistically, an electrophilic spirocyclization followed by C−C migration explains the formation of rearranged products.
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spelling pubmed-94015782022-08-26 Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions Shi, Peng Tu, Yongliang Kong, Deshen Wu, Peng Ma, Ding Bolm, Carsten Angew Chem Int Ed Engl Communications In a ball mill, FeBr(3)‐catalyzed intramolecular amidations lead to 3,4‐dihydro‐2(1H)‐quinolinones in good to almost quantitative yields. The reactions do not require a solvent and are easy to perform. No additional ligand is needed for the iron catalyst. Both 4‐substituted aryl and β‐substituted dioxazolones provide products with high selectivity. Mechanistically, an electrophilic spirocyclization followed by C−C migration explains the formation of rearranged products. John Wiley and Sons Inc. 2022-06-10 2022-07-25 /pmc/articles/PMC9401578/ /pubmed/35511087 http://dx.doi.org/10.1002/anie.202204874 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Shi, Peng
Tu, Yongliang
Kong, Deshen
Wu, Peng
Ma, Ding
Bolm, Carsten
Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title_full Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title_fullStr Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title_full_unstemmed Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title_short Iron‐Catalyzed Intramolecular Arene C(sp(2))−H Amidations under Mechanochemical Conditions
title_sort iron‐catalyzed intramolecular arene c(sp(2))−h amidations under mechanochemical conditions
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401578/
https://www.ncbi.nlm.nih.gov/pubmed/35511087
http://dx.doi.org/10.1002/anie.202204874
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AT kongdeshen ironcatalyzedintramoleculararenecsp2hamidationsundermechanochemicalconditions
AT wupeng ironcatalyzedintramoleculararenecsp2hamidationsundermechanochemicalconditions
AT mading ironcatalyzedintramoleculararenecsp2hamidationsundermechanochemicalconditions
AT bolmcarsten ironcatalyzedintramoleculararenecsp2hamidationsundermechanochemicalconditions

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