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Synfacts 2018; 14(06): 0649
DOI: 10.1055/s-0037-1609962
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Pt-Catalyzed Chemoselective Hydrogenation of Dienes and Nitroarenes

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Camacho-Bunquin J. * Ferrandon M. Sohn H. Yang D. Liu C. de Leon PA. I. Perras FA. Pruski M. Stair PC. * Delferro M. * Argonne National Laboratory, Lemont, U.S. Department of Energy and Iowa State University, Ames, and Northwestern University, Evanston, USA
Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica.

J. Am. Chem. Soc. 2018;
140: 3940−3951
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Publication History

Publication Date:
17 May 2018 (online)

 
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Key words

hydrogenation - chemoselectivity - nitroarenes - platinum catalysis

Significance

An organoplatinum(IV) catalyst supported on Zn(II)-modified SiO2 [(MeCp)PtH/Zn/SiO2], prepared as shown in equation 1, catalyzed the semihydrogenation of buta-1,3-diene under H2 to afford butenes in 86% conversion with 89% mono-olefin selectivity (eq. 2). The catalyst also promoted the chemoselective hydrogenation of nitrobenzenes bearing various reducible substituents, such as alkene, nitrile, or carbonyl groups, to afford the corresponding anilines in up to >99% conversion and up to >99% selectivity, with the substituents remaining intact (eq. 3).


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Comment

The catalyst was characterized by means of solid-state NMR, XANES, EXAFS, ­PXRD, HR-TEM, TPR-H2, NH3-TPD, DRIFTS, DRUV-vis, and elemental analyses. In the hydrogenation of nitrobenzene, the catalyst was recovered by decantation and reused twice without loss of its catalytic activity.


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