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Preparation of substituted anilines from nitro compounds by using supported gold catalysts

Abstract

A protocol for the chemoselective hydrogenation of nitro compounds to the corresponding anilines by means of supported gold catalysts is described. Nitro groups on different compounds — containing double bonds, carbonyl, nitrile or amide groups — have been successfully hydrogenated on supported gold nanoparticles (Au/TiO2 and Au/Fe2O3), using a batch reactor under H2 pressure. Unlike other noble metals, gold shows high chemoselectivity towards reduction of the nitro group, at near-complete conversion of the substrate. The total time to carry out this protocol strongly depends on the reaction step, which is a function of the activity of the catalyst and the nature of the substrate.

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Figure 1: Schematic of the synthesis of several substituted amino compounds.
Figure 2: The SPR16 reactor from AMTEC.

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References

  1. Bae, J.W., Cho, Y.J., Lee, S.H. & Toon, C.M. Chemoselective reduction of nitroaromatics to anilines using decaborane in methanol. Tetrahedron Lett., 41, 175–177 (2000).

    Article  CAS  Google Scholar 

  2. Li, C.-H. et al. Nitrobenzene hydrogenation with carbon nanotube-supported platinum catalyst under mild conditions. J. Mol. Catal. A: Chem. 226, 101–105 (2005).

    Article  CAS  Google Scholar 

  3. Gowda, S. & Gowda, D.C. Application of hydrazinium monoformate as new hydrogen donor with Raney nickel: a facile reduction of nitro and nitrile moieties. Tetrahedron 58, 2211–2213 (2002).

    Article  CAS  Google Scholar 

  4. Toti, A. et al. Hydrogenation of single and multiple N–N or N–O bonds by Ru(II) catalysts in homogeneous phase. J. Organomet. Chem. 690, 3641–3651 (2005).

    Article  CAS  Google Scholar 

  5. Kovar, R.F. & Arnold, F.E. Ethynyl-substituted aromatic ortho diamines and method of synthesis. U.S. Patent 3,975,444 to the U.S. Air Force. (1976).

  6. Suchy, M., Winternitz, P. & Zeller, M. Herbicidal compositions comprising 3-aryluracyl derivative as active ingredient and process for producing for producing the active ingredient. WO Patent 91/00278 to Ciba-Geigy. (1991).

  7. Butera, J. & Bagli, J. n-Heteroaralkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing class iii antiarrhythmic activity. WO Patent 91/09023 to American Home Products. (1991).

  8. Burawoy, A. & Critchley, J.P. Electronic spectra of organic molecules and their interpretation V: Effect of terminal groups containing multiple bonds on the K-bands of conjugated systems. Tetrahedron 5, 340 (1959).

    Article  CAS  Google Scholar 

  9. Braden, R., Knupfer, H. & Hartung, S. Process for the preparation of unsaturated amino compounds. U.S. Patent 4,002,673 to Bayer AG. (1977).

  10. Braden, R., Knupfer, H. & Hartung, S. Process for the preparation of unsaturated amino compounds. U.S. Patent 4,051,177 to Bayer AG. (1977).

  11. Narendra, M.A., Shivanand, O.P. & Madhukar, D.R. Selective hydrogenation of nitrogen containing aromatics WO Patent 2005.070.869 to Council Scient. Ind. Res. (2005).

  12. Blaser, H.U., Siegrist, U., Steiner, H. & Studer, M. Aromatic Nitro Compounds. Fine Chemicals Through Heterogeneous Catalysis (eds. Sheldon, R.A., van Bekkum, H.) 389–406 (Wiley-VCH, Weinheim, Germany, 2001).

    Google Scholar 

  13. Corma, A. & Serna, P. Chemoselective hydrogenation of nitro compounds with supported gold catalysts. Science 313, 332 (2006).

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support from the Spanish government (Project MAT 2003-07945-C02-01, and grant FPU AP2003-4635) and the EU Commission (TOPCOMBI Project) is gratefully acknowledged.

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Correspondence to Avelino Corma.

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Corma, A., Serna, P. Preparation of substituted anilines from nitro compounds by using supported gold catalysts. Nat Protoc 1, 2590–2595 (2006). https://doi.org/10.1038/nprot.2006.441

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