Reduction of nitrobenzene derivatives using sodium borohydride and transition metal sulfides

Abstract Reported here is the reduction of aromatic nitro compounds using sodium borohydride and transition metal sulfides as catalysts. The reaction conditions were optimized using the reduction of nitrobenzene as a model reaction. The catalysts studied were iron sulfide (Fe 3 S 4 ), copper sulfide (CuS), zinc sulfide (ZnS), cobalt sulfide (Co 3 S 4 ), and nickel sulfide (NiS). The reduction was monitored using gas chromatography. Quantitative conversions were achieved using Co 3 S 4 and NiS, representing a ten-fold increase in reactivity compared to the non-catalyzed reaction. Fe 3 S 4 and ZnS had no apparent effect on the reduction of nitrobenzene while the reduction using CuS showed a marginal increase. The reduction method was applied to several aryl-nitro derivatives containing either electron-withdrawing or electron-donating groups. Halogen containing aryl-nitro compounds were reduced without dehalogenation. The reduction had no effect on other functional groups such as carboxylic acids, esters, amides, or alkenes, indicating that the reduction is highly chemoselective.