4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen

4-N,N-Dimethylaminopyridine (DMAP) as catalyst in combination with benzyl bromide was developed for the selective oxidation of methyl aromatics. DMAP exhibited higher catalytic activity than other pyridine analogues, such as 4-carboxypyridine, 4-cyanopyridine and pyridine. The sp(3) hybrid carbon-hy...

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Detalles Bibliográficos
Autores principales: Zhang, Zhan, Gao, Jin, Wang, Feng, Xu, Jie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268158/
https://www.ncbi.nlm.nih.gov/pubmed/22466855
http://dx.doi.org/10.3390/molecules17043957
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author Zhang, Zhan
Gao, Jin
Wang, Feng
Xu, Jie
author_facet Zhang, Zhan
Gao, Jin
Wang, Feng
Xu, Jie
author_sort Zhang, Zhan
collection PubMed
description 4-N,N-Dimethylaminopyridine (DMAP) as catalyst in combination with benzyl bromide was developed for the selective oxidation of methyl aromatics. DMAP exhibited higher catalytic activity than other pyridine analogues, such as 4-carboxypyridine, 4-cyanopyridine and pyridine. The sp(3) hybrid carbon-hydrogen (C–H) bonds of different methyl aromatics were successfully oxygenated with molecular oxygen. The real catalyst is due to the formation of a pyridine onium salt from the bromide and DMAP. The onium salt was well characterized by NMR and the reaction mechanism was discussed.
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spelling pubmed-62681582018-12-11 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen Zhang, Zhan Gao, Jin Wang, Feng Xu, Jie Molecules Communication 4-N,N-Dimethylaminopyridine (DMAP) as catalyst in combination with benzyl bromide was developed for the selective oxidation of methyl aromatics. DMAP exhibited higher catalytic activity than other pyridine analogues, such as 4-carboxypyridine, 4-cyanopyridine and pyridine. The sp(3) hybrid carbon-hydrogen (C–H) bonds of different methyl aromatics were successfully oxygenated with molecular oxygen. The real catalyst is due to the formation of a pyridine onium salt from the bromide and DMAP. The onium salt was well characterized by NMR and the reaction mechanism was discussed. MDPI 2012-03-30 /pmc/articles/PMC6268158/ /pubmed/22466855 http://dx.doi.org/10.3390/molecules17043957 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Communication
Zhang, Zhan
Gao, Jin
Wang, Feng
Xu, Jie
4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title_full 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title_fullStr 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title_full_unstemmed 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title_short 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen
title_sort 4-n,n-dimethylaminopyridine promoted selective oxidation of methyl aromatics with molecular oxygen
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268158/
https://www.ncbi.nlm.nih.gov/pubmed/22466855
http://dx.doi.org/10.3390/molecules17043957
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AT wangfeng 4nndimethylaminopyridinepromotedselectiveoxidationofmethylaromaticswithmolecularoxygen
AT xujie 4nndimethylaminopyridinepromotedselectiveoxidationofmethylaromaticswithmolecularoxygen

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