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Issue 5, 2016
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Chemoselective nitro reduction and hydroamination using a single iron catalyst

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Abstract

The reduction and reductive addition (formal hydroamination) of functionalised nitroarenes is reported using a simple and bench-stable iron(III) catalyst and silane. The reduction is chemoselective for nitro groups over an array of reactive functionalities (ketone, ester, amide, nitrile, sulfonyl and aryl halide). The high activity of this earth-abundant metal catalyst also facilitates a follow-on reaction in the reductive addition of nitroarenes to alkenes, giving efficient formal hydroamination of olefins under mild conditions. Both reactions offer significant improvements in catalytic activity and chemoselectivity and the utility of these catalysts in facilitating two challenging reactions supports an important mechanistic overlap.

Graphical abstract: Chemoselective nitro reduction and hydroamination using a single iron catalyst

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Supplementary files

Article information


Submitted
20 Nov 2015
Accepted
24 Jan 2016
First published
26 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 3031-3035
Article type
Edge Article

Chemoselective nitro reduction and hydroamination using a single iron catalyst

K. Zhu, M. P. Shaver and S. P. Thomas, Chem. Sci., 2016, 7, 3031
DOI: 10.1039/C5SC04471E

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