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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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Publication details

The article was received on 20 Nov 2015, accepted on 24 Jan 2016 and first published on 26 Jan 2016


Article type: Edge Article
DOI: 10.1039/C5SC04471E
Citation: Chem. Sci., 2016,7, 3031-3035
  • Open access: Creative Commons BY-NC license
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    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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