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Molecules 2012, 17(4), 3957-3968; doi:10.3390/molecules17043957
Communication

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

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Received: 2 March 2012; in revised form: 23 March 2012 / Accepted: 27 March 2012 / Published: 30 March 2012
(This article belongs to the Special Issue Organocatalysis)
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Abstract: 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 sp3 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.
Keywords: organocatalysis; selective oxidation; methyl aromatics; molecular oxygen; 4-N,N-dimethylaminopyridine organocatalysis; selective oxidation; methyl aromatics; molecular oxygen; 4-N,N-dimethylaminopyridine
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zhang, Z.; Gao, J.; Wang, F.; Xu, J. 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen. Molecules 2012, 17, 3957-3968.

AMA Style

Zhang Z, Gao J, Wang F, Xu J. 4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen. Molecules. 2012; 17(4):3957-3968.

Chicago/Turabian Style

Zhang, Zhan; Gao, Jin; Wang, Feng; Xu, Jie. 2012. "4-N,N-Dimethylaminopyridine Promoted Selective Oxidation of Methyl Aromatics with Molecular Oxygen." Molecules 17, no. 4: 3957-3968.



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