Abstract
The catalytic hydrogenation of nitroarenes is an environmentally benign technology for the production of anilines, which are key intermediates for manufacturing agrochemicals, pharmaceuticals and dyes. Most of the precious metal catalysts, however, suffer from low chemoselectivity when one or more reducible groups are present in a nitroarene molecule. Herein we report FeOx-supported platinum single-atom and pseudo-single-atom structures as highly active, chemoselective and reusable catalysts for hydrogenation of a variety of substituted nitroarenes. For hydrogenation of 3-nitrostyrene, the catalyst yields a TOF of ~1,500 h(-1), 20-fold higher than the best result reported in literature, and a selectivity to 3-aminostyrene close to 99%, the best ever achieved over platinum group metals. The superior performance can be attributed to the presence of positively charged platinum centres and the absence of Pt-Pt metallic bonding, both of which favour the preferential adsorption of nitro groups.
Highlights
The catalytic hydrogenation of nitroarenes is an environmentally benign technology for the production of anilines, which are key intermediates for manufacturing agrochemicals, pharmaceuticals and dyes
Through modification of transition metal with well-chosen additives, for example, Pt/ C-H3PO2-VO(acac)[2] and Pt-Pb/CaCO3-FeCl2-nBu4NCl, chemo selective reduction of nitroarenes was obtained at the expense of activity[4]
Noble metalfree catalysts based on cobalt– or iron–phenanthroline complexes have been developed for the chemoselective hydrogenation of nitroarens, with excellent chemoselectivities for numerous structurally diverse substrates[17,18], but similar to the IB-group metals they require relatively demanding reaction conditions, for example, long reaction time, high temperature (120 °C) and high H2 pressure (50 bar)
Summary
The catalytic hydrogenation of nitroarenes is an environmentally benign technology for the production of anilines, which are key intermediates for manufacturing agrochemicals, pharmaceuticals and dyes. In this study we report that FeOx-supported Pt single-atom and pseudo-single-atom structures are extremely active, chemoselective and recyclable for the hydrogenation of a variety of functionalized nitroarenes.
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