Chemoselective nitro reduction and hydroamination using a single iron catalyst

Chemical Science
Kailong ZhuStephen P Thomas

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.

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Citations

Dec 24, 2018·Angewandte Chemie·Samuel Suárez-PantigaRoberto Sanz
Jul 22, 2020·Chemical Communications : Chem Comm·Ni ShenJun-An Ma
Jul 21, 2017·Angewandte Chemie·Marian RauserMeike Niggemann
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Mar 21, 2019·Angewandte Chemie·Yongtao XieZhengming Li
Oct 24, 2020·Chemical Communications : Chem Comm·Yang GaoXiao-Qiang Hu
Feb 2, 2021·Chemical Science·Sophia L ShevickRyan A Shenvi
Jan 22, 2021·Angewandte Chemie·Anup BhuniaArmido Studer
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Methods Mentioned

BETA
hydroamination

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