Go Nitro: To Stand Divided: 2

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j) H. I. Schlesinger, H. C. Brown, E. Finholt, J. R. Gilbreath, H. R. Hoekstra and E. Hyde, J. Am. Chem. Soc., 1953, 75, 215 CrossRef CAS; a) CAS Scifinder® summarizes around 500 research reports for past 5 years (2009–2014) on the topic “Reduction of Nitrobenzene”;

K. A. Reza, Z. Maryam, M. T. Fatemeh and F. M. Mehdi, Iran. J. Chem. Chem. Eng., 2011, 30, 37 Search PubMed.

D. M. Dotzauer, S. Bhattacharjee, Y. Wen and M. L. Bruening, Langmuir, 2009, 25, 1865 CrossRef CAS PubMed. A novel iodide-catalyzed reduction method using hypophosphorous and/or phosphorous acids was developed by Wu et al. to reduce both diaryl ketones and nitroarenes chemoselectively in the presence of chloro and bromo substituents in high yields. 84 This efficient and practical method has been successfully applied to large-scale production of a potential anticancer agent, lonafarnib. b) L. He, L. Wang, H. Sun, J. Ni, Y. Cao, H. He and K. Fan, Angew. Chem., Int. Ed., 2009, 48, 9538 CrossRef CAS PubMed.

Iron oxide hydroxide catalyst was used for reduction of nitroarenes to anilines with polymer (D113, macroporous weak acidic ion-exchange resin)-supported hydrazine hydrate in refluxing isopropanol by Shi and coworkers. 66 Anilines were obtained in 93 to 99% yields without chlorides and esters being affected. g) G. Wienhofer, I. Sorribes, A. Boddien, F. Westerhaus, K. Junge, H. Junge, R. Llusar and M. Beller, J. Am. Chem. Soc., 2011, 133, 12875 CrossRef PubMed; c) J. W. Larsen, M. Freund, K. Y. Kim, M. Sidovar and J. L. Stuart, Carbon, 2000, 38, 655 CrossRef CAS. Hyperbranched polyamidoamine (PAMAM) dendrimers were grafted on a graphite surface and Ag NPs were synthesized within the graphite-grafted PAMAM dendrimer templates and applied as a nanocatalyst for the reduction of nitroaromatics by Rajesh and Venkatesan. 51 The efficiency of this system has been demonstrated through the reduction of halonitroarenes without dehalogenation in the halogeno-substituted nitrobenzenes and selective reduction of nitro groups in the presence of imine functionality under mild conditions.

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A magnetically separable gold-nanoparticle catalyst was prepared and it showed excellent activity for chemoselective reduction of nitroarenes with hydrosilanes. 61 Selective reduction of 4-fluoro- and 4-chloronitrobenzene required only 1 mol% Au while 40 mol% was required for complete reduction of 4-bromonitrobenzene, and 4-iodonitrobenzene could not be reduced. Ketone, ester, amide, cyano, alkene, benzyloxy and carbobenzyloxy functional groups survived during nitro reduction. The activity of the catalyst reduced during its reuse but increasing the quantity of reducing agent could compensate for this reduced activity. a) J. F. Quinn, C. E. Bryant, K. C. Golden and B. T. Gregg, Tetrahedron Lett., 2010, 51, 786 CrossRef CAS PubMed;