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  • 4-N,N-Dimethylaminopyridine promoted selective oxidation of methyl aromatics with molecular oxygen.

4-N,N-Dimethylaminopyridine promoted selective oxidation of methyl aromatics with molecular oxygen.

Molecules (Basel, Switzerland) (2012-04-03)
Zhan Zhang, Jin Gao, Feng Wang, Jie Xu
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-(Dimethylamino)pyridine, ReagentPlus®, ≥99%
Sigma-Aldrich
Benzyl bromide, reagent grade, 98%
Sigma-Aldrich
4-(Dimethylamino)pyridine, purum, ≥98.0% (NT)