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Molecules 2011, 16(5), 3563-3568; doi:10.3390/molecules16053563

Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water

1, 2,* , 1, 1, 1 and 3
1 School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China 2 School of Science, Beijing Jiaotong University, Beijing 100044, China 3 Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL 62026, USA
* Author to whom correspondence should be addressed.
Received: 24 February 2011 / Revised: 15 April 2011 / Accepted: 22 April 2011 / Published: 28 April 2011
(This article belongs to the Section Organic Synthesis)
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The synthesis of the azoxybenzenes by the reduction of nitroarenes with reducing agent potassium borohydride in water was reported for the first time. PEG-400 was used as a phase transfer catalyst and could effectively catalyze the reduction. The electronic effects of substituent groups play an important role in determining the reduction efficiencies. Electron-withdrawing substituents promote the formation of the azoxybenzene products, while electron-releasing groups retard the reductions to various degrees depending on the extent of their electron-donating ability.
Keywords: nitroarenes; azoxybenzenes; potassium borohydride; water; PEG-400 nitroarenes; azoxybenzenes; potassium borohydride; water; PEG-400
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Liu, Y.; Liu, B.; Guo, A.; Dong, Z.; Jin, S.; Lu, Y. Reduction of Nitroarenes to Azoxybenzenes by Potassium Borohydride in Water. Molecules 2011, 16, 3563-3568.

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