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Synfacts 2013; 9(1): 0111
DOI: 10.1055/s-0032-1317912
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reduction of Nitroarenes Using In Situ Generated Iron Oxide Nanocrystals

Contributor(s):
Yasuhiro Uozumi
,
Fumie Sakurai
Cantillo D, Baghbanzadeh M, Kappe CO * Karl-Franzens-University, Graz, Austria
In Situ Generated Iron Oxide Nanocrystals as Efficient and Selective Catalysts for the Reduction of Nitroarenes Using a Continuous Flow Method.

Angew. Chem. Int. Ed. 2012;
51: 10190-10193
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

iron - nanoparticles - nitroarenes - reduction - flow reaction

Significance

Iron oxide nanocrystals, generated in situ from Fe(acac)3 and hydrazine hydrate, catalyzed the reduction of nitroarenes with hydrazine hydrate under microwave conditions to give the corresponding anilines in 95–99% yield (20 examples, eq. 1). In the reduction of nitrobenzene to aniline using the batch system, the catalyst was magnetically separated from the reaction mixture and reused seven times.


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Comment

The reduction of nitroarenes was also performed using a continuous-flow system to afford the anilines in 95−97% yield (eq. 2). The in situ generated iron oxide nanoparticles were characterized by XRD and HRTEM analyses. ICP–MS showed 7.9% iron leaching from the catalyst during the reduction using the batch system.


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