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Insight into the mechanism of gold-catalyzed reduction of nitroarenes based on the substituent effect and in situ IR

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Abstract

A study is presented here on the mechanistic pathway of catalytic reduction of nitroarenes with diverse substituent groups in the presence of ultra-small gold nanoparticles and NaBH4. The kinetic data based on the substituent effect and the Hammett plot, together with analyses of intermediates, revealed that this reaction followed a direct route and that all of the reaction steps were rapid without accumulation of intermediates. In particular, in situ IR was found to be an effective method for the real-time monitoring of this model reduction in our catalytic system and confirmed the presence of a hydroxylamine intermediate. These results will provide a new insight into the mechanism of gold-catalyzed reduction of nitroarenes and offer a reference for future mechanism tests of heterogeneous nanocatalysis.

Graphical abstract: Insight into the mechanism of gold-catalyzed reduction of nitroarenes based on the substituent effect and in situ IR

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Publication details

The article was received on 13 Jan 2017, accepted on 10 Apr 2017 and first published on 11 Apr 2017


Article type: Paper
DOI: 10.1039/C7NJ00157F
Citation: New J. Chem., 2017, Advance Article
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    Insight into the mechanism of gold-catalyzed reduction of nitroarenes based on the substituent effect and in situ IR

    C. Wang, W. Zou, J. Wang, Y. Ge, R. Lu and S. Zhang, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ00157F

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