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Synfacts 2010(4): 0492-0492  
DOI: 10.1055/s-0029-1219464
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Reduction of Nitroarenes with Hydrogen Transfer Catalysis

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
J. F. Quinn*, C. E. Bryant, K. C. Golden, B. T. Gregg
Albany Molecular Research, Inc., New York, USA
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

The reduction of nitroarenes to the corresponding anilines via hydrogen transfer catalysis was described. Thus, the catalytic reduction of nitroarenes 1a-f was carried out with 1,4-cyclohexadiene (2) as a hydrogen transfer source to give the corresponding anilines 3a-f in 70-99% yield. The Pd/C-catalyzed hydrogenation of the chloro-substituted nitroarenes 1g,h gave aniline (4) and 3-aminopyridine (5) in 99% yield, while the Pt/C-mediated reduction gave 4-chloroaniline (3g) and 3-amino-2-chloropyridine (3h) with good selectivity (3g/4 = 75:25, 3h/5 = 79:19).