Synfacts 2017; 13(10): 1095
DOI: 10.1055/s-0036-1591291
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Chemoselective Hydrogenation of Functionalized Nitroarenes to Anilines

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Aya Ohno
Wei H. Ren Y. Wang A. * Liu X. Liu X. Zhang L. Miao S. Li L. Liu J. Wang J. Wang G. Su D. Zhang T. * Dalian Institute of Chemical Physics, University of Chinese Academy of Science, Beijing, and Institute of Coal Chemistry, Taiyuan, P. R. of China; Arizona State University, Tempe, USA
Remarkable Effect of Alkalis on the Chemoselective Hydrogenation of Functionalized Nitroarenes over High-Loading Pt/FeOx Catalysts.

Chem. Sci. 2017;
8: 5126-5131
Further Information

Publication History

Publication Date:
18 September 2017 (online)

 
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Significance

A sodium-containing FeOx-supported platinum catalyst (Na-Pt/FeOx) was prepared by mixing H2PtCl6 and Fe(NO3)3 with (NH4)2CO3 in water, followed by the treatment with NaNO3, calcination, and reduction with hydrogen (eq.1). Na-Pt/FeOx catalyzed the chemoselective hydrogenation of substituted nitroarenes under hydrogen pressure to afford the corresponding anilines in 95–97% yield (eq. 2). In the hydrogenation of 3-nitrostyrene, Na-Pt/FeOx promoted the hydrogenation of the nitro group to give 3-aminostyrene in 95% conversion with 98% selectivity (eq. 3). The catalyst was reused three times without significant loss of its catalytic activity or chemoselectivity.


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Comment

Other alkali-metal-containing Pt/FeOx catalysts (Li-Pt/FeOx and K-Pt/FeOx) also promoted the selective hydrogenation of 3-nitrostyrene to 3-aminostyrene in 96 to >99% conversion and 94–95% selectivity. Compared with alkali-metal-containing catalysts, alkali-metal-free Pt/FeOx showed a lower selectivity (99% conversion and 66% selectivity). The authors have previously reported the chemoselective hydrogenation of functionalized nitroarenes to the corresponding anilines by using FeOx-supported platinum catalysts prepared from H2PtCl6, Fe(NO3)3, and Na2CO3 (Nat. Commun. 2014, 5, 5634).


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