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Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes

In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe–Fe(3)C nanoparticles and Fe–N(x) sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes usi...

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Detalles Bibliográficos
Autores principales: Ma, Zhiming, Song, Tao, Yuan, Youzhu, Yang, Yong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6984390/
https://www.ncbi.nlm.nih.gov/pubmed/32110314
http://dx.doi.org/10.1039/c9sc04060a
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author Ma, Zhiming
Song, Tao
Yuan, Youzhu
Yang, Yong
author_facet Ma, Zhiming
Song, Tao
Yuan, Youzhu
Yang, Yong
author_sort Ma, Zhiming
collection PubMed
description In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe–Fe(3)C nanoparticles and Fe–N(x) sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H(2)O(2) as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe–N(x) sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles.
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spelling pubmed-69843902020-02-27 Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes Ma, Zhiming Song, Tao Yuan, Youzhu Yang, Yong Chem Sci Chemistry In this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe–Fe(3)C nanoparticles and Fe–N(x) sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H(2)O(2) as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones were synthesized in high yields with a broad substrate scope and good tolerance of functional groups. Characterization and control experiments disclose that a synergistic effect between the metallic Fe nanoparticles and built-in Fe–N(x) sites is primarily responsible for the outstanding catalytic performance. Furthermore, the iron nanocomposite could be readily recovered for successive use without appreciable loss in catalytic activity and selectivity. This work provides an expedient and sustainable method to access pharmaceutically relevant N-heterocycles. Royal Society of Chemistry 2019-09-23 /pmc/articles/PMC6984390/ /pubmed/32110314 http://dx.doi.org/10.1039/c9sc04060a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Ma, Zhiming
Song, Tao
Yuan, Youzhu
Yang, Yong
Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title_full Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title_fullStr Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title_full_unstemmed Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title_short Synergistic catalysis on Fe–N(x) sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
title_sort synergistic catalysis on fe–n(x) sites and fe nanoparticles for efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6984390/
https://www.ncbi.nlm.nih.gov/pubmed/32110314
http://dx.doi.org/10.1039/c9sc04060a
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