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Chemoselective nitro reduction and hydroamination using a single iron catalyst

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 an...

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Detalles Bibliográficos
Autores principales: Zhu, Kailong, Shaver, Michael P., Thomas, Stephen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6005157/
https://www.ncbi.nlm.nih.gov/pubmed/29997793
http://dx.doi.org/10.1039/c5sc04471e
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author Zhu, Kailong
Shaver, Michael P.
Thomas, Stephen P.
author_facet Zhu, Kailong
Shaver, Michael P.
Thomas, Stephen P.
author_sort Zhu, Kailong
collection PubMed
description 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.
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spelling pubmed-60051572018-07-11 Chemoselective nitro reduction and hydroamination using a single iron catalyst Zhu, Kailong Shaver, Michael P. Thomas, Stephen P. Chem Sci Chemistry 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. Royal Society of Chemistry 2016-05-01 2016-01-26 /pmc/articles/PMC6005157/ /pubmed/29997793 http://dx.doi.org/10.1039/c5sc04471e Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Zhu, Kailong
Shaver, Michael P.
Thomas, Stephen P.
Chemoselective nitro reduction and hydroamination using a single iron catalyst
title Chemoselective nitro reduction and hydroamination using a single iron catalyst
title_full Chemoselective nitro reduction and hydroamination using a single iron catalyst
title_fullStr Chemoselective nitro reduction and hydroamination using a single iron catalyst
title_full_unstemmed Chemoselective nitro reduction and hydroamination using a single iron catalyst
title_short Chemoselective nitro reduction and hydroamination using a single iron catalyst
title_sort chemoselective nitro reduction and hydroamination using a single iron catalyst
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6005157/
https://www.ncbi.nlm.nih.gov/pubmed/29997793
http://dx.doi.org/10.1039/c5sc04471e
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AT shavermichaelp chemoselectivenitroreductionandhydroaminationusingasingleironcatalyst
AT thomasstephenp chemoselectivenitroreductionandhydroaminationusingasingleironcatalyst