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Synfacts 2020; 16(03): 0317
DOI: 10.1055/s-0039-1691726
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Shape-Selective Hydrogenation of Nitroarenes by Using Zeolite-Encaged Single-Atom Rhodium Catalysts

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Sun Q, Wang N, Zhang T, Bai R, Mayoral A. * Zhang P, Zhang Q, Terasaki O, Yu J. * ShanghaiTech University and Jilin University, Changchun, P. R. of China
Zeolite-Encaged Single-Atom Rhodium Catalysts: Highly-Efficient Hydrogen Generation and Shape-Selective Tandem Hydrogenation of Nitroarenes.

Angew. Chem. Int. Ed. 2019;
58: 18570-18576
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Publication History

Publication Date:
18 February 2020 (online)

 
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Key words

rhodium catalysis - reduction - nitroarenes - ammonia–borane - anilines

Significance

A single-atom rhodium catalyst immobilized on silicate-1 zeolite (Rh@S-1-H), prepared as shown in equation 1, catalyzed the hydrolysis of ammonia–borane with a turnover frequency of 432 molH2 molRh –1 min–1 (eq. 2). A sequential hydrolysis of ammonia–borane and ­hydrogenation of nitroarenes also proceeded in the presence of Rh@S-1-H (eq. 3).


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Comment

As shown in equation 3, p-substituted nitrobenzenes were reduced to the corresponding anilines with 100% conversion and >99% selectivity, whereas m-substituted nitrobenzenes were almost intact after the hydrogenation reaction. Rh@S-1-H was characterized by means of 13C MAS-NMR, TG-DTA, PXRD, ICP-AES, HAADF-STEM, HRTEM, SEM, EDS, XPS, XANES, EXAFS, and CO-DRIFTS measurements.


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