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Tandem Selective Reduction of Nitroarenes Catalyzed by Palladium Nanoclusters

Abstract

We report a catalytic tandem reduction of nitroarenes by sodium borohydride (NaBH4) in aqueous solution at ambient conditions, which can selectively produce five categories of nitrogen-containing compounds: anilines, N-aryl hydroxylamines, azoxy-, azo- and hydrazo- compounds. The catalyst is the in situ-generated ultrasmall palladium nanoclusters (Pd NCs, diameter of 1.3±0.3 nm) from the reduction of Pd(OAc)2 by NaBH4. These highly active Pd NCs are stabilized by the surface-coordinated nitroarenes, which inhibit the further growth and aggregation of Pd NCs. By controlling the concentration of Pd(OAc)2 (0.1-0.5 mol% of nitroarene) and NaBH4, the water/ethanol solvent ratio and the tandem reaction sequence, each of the five categories of N-containing compounds can be obtained with excellent yields (up to 98%) in less than 30 min at room temperature. This tunable catalytic tandem reaction works efficiently with a broad range of nitroarene substrates, which offers a green and sustainable method for rapid and large-scale production of valuable N-containing chemicals.

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Supplementary files

Article information


Submitted
17 Nov 2019
Accepted
15 Jan 2020
First published
15 Jan 2020

Green Chem., 2020, Accepted Manuscript
Article type
Paper

Tandem Selective Reduction of Nitroarenes Catalyzed by Palladium Nanoclusters

Z. Yan, X. Xie, Q. Song, F. Ma, X. Sui, Z. Huo and M. Ma, Green Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9GC03957K

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