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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

1,2
,
1
,
1
 and
1,*
1 State Key Laboratory of Catalysis, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China 2 Graduate university of Chinese Academy of Sciences, Beijing 100049, China
* Author to whom correspondence should be addressed.
Received: 2 March 2012 / Revised: 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 (CC BY 3.0).

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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.

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