Simple, Practical and Eco-friendly Reduction of Nitroarenes with Zinc in the Presence of olyethylene Glycol Immobilized on Silica Gel as a New Solid–liquid Phase Transfer Catalyst in Water

Document Type: Research Note

Authors

1 Department of Chemistry, Faculty of Science, Shahid Chamran University, P.O. Box 61357-4-3169 Ahvaz, I.R. IRAN

2 Department of Marine Chemistry, Khoramshahr Marine Science & Technology University, Khoramshahr, I.R. IRAN

Abstract

Polyethylene glycol was easily grafted to silica gel and used as a solid–liquid phase transfer catalyst in the reduction of aromatic nitro compounds. This silica-grafted polyethylene glycol is proved to be an efficient heterogeneous catalyst in the reduction of nitroarenes to the corresponding aromatic amines with zinc powder in water. The reduction reactions proceeded efficiently with excellent chemoselectivity without affecting other sensitive functional groups.

Keywords

Main Subjects


[1] Starks C.M., Liotta C.L., Halpern M., "Phase-Transfer Catalysis, Fundamental, Applications, and Industrial Perspectives", Chapman & Hall, New York, (1994).

[2] Sun H., Li J., Cai X.C., Jiang D., Dai L.Y., Ionic Liquids as Efficient Phase-Transfer Catalysts for the Solid Base-Promoted Monoalkylation of Diethyl Malonate, Chin. Chem. Lett., 18, p. 279 (2007).

[3] Keller W.E., "Phase Transfer Reactions", Fluka-Compendium, 3, Georg Thime Verlag,Stuttgart, (1992).

[5] Smith G.V., Nothesiz F., "Heterogeneous Catalysis in Organic Chemistry", Academic Press,New York, (1999).

[6] Scheuerman R.A., Tumelty D., The Reduction of Aromatic Nitro Groups on Solid Supports Using Sodium Hydrosulfite (Na2S2O4), Tetrahedron Lett. 41, p. 6531 (2000).

[7] Banik B.K., Mukhopadhyay C., Venkattman M.S., Becker F.F., A Facile Reduction of Aromatic Nitro Compounds to Aromatic Amines by Samarium and Iodine, Tetrahedron Lett. 39, p. 7243 (1998).

[8] Cho Y.S., Jun B.K., Kim S., Cha J.H., Pae A.N., Koh H.Y., Chang M.H., Han S.Y., Reduction of Nitro Group Using Indium-wire in Water, Bull. Korean Chem. Soc. 24, p. 653 (2003).

[9] Kumar J.S.D., Ho M.M., Toyokuni T., Simple and Chemoselective Reduction of Aromatic Nitro Compounds to Aromatic Amines: Reduction with Hydriodic Acid Revisited, Tetrahedron Lett., 42, p. 5601 (2001).

[10] Mdleleni M.M., Rinker R.G., Ford P.C., Reduction of Aromatic Nitro Compounds as Catalyzed by Rhodium Trichloride under Water-Gas Shift Reaction Conditions, J. Mol. Catal. A: Chem., 204-205, p. 125 (2003).

[11] Chen Y., Qiu J., Wang X., Xiu J., Preparation and Application of Highly Dispersed Gold Nanoparticles Supported on Silica for Catalytic Hydrogenation of Aromatic Nitro Compounds, J. Catal., 242, p. 227 (2006).

[13] Ghosh S.K., Mandal M., Kundu S., Nath S., Pal T., Bimetallic Pt–Ni Nanoparticles Can Catalyze Reduction of Aromatic Nitro Compounds by Sodium Borohydride in Aqueous Solution, Appl. Catal. A: Gen., 268, p. 61 (2004).

[14] Ren P.D., Pan S.F., Dang T.W., Wu H.S., The Novel Reduction Systems: NaBH4-SbCl3 OR NaBH4-BiCl3 for Conversion of Nitroarenes to Primary Amines, Synth. Commun. 25, p. 3799 (1995).

[15] Nagaraja D., Pasha M.A., Reduction of Aryl Nitro Compounds with Aluminium/NH4Cl: Effect of Ultrasound on the Rate of the Reaction, Tetrahedron Lett., 40, p. 7855 (1999).

[16] Kiasat A.R., Fallah-Mehrjardi M., Polyethylene Glycol: A Cheap and Efficient Medium for the Thiocyanation of Alkyl Halides, Bull. Korean Chem. Soc. 29, p. 2346 (2008).

[19] Kiasat  A.R.,  Fallah-Mehrjardi  M.,  B(HSO4)3: A Novel and Efficient Solid Acid Catalyst for the Regioselective Conversion of Epoxides to Thiocyanohydrins Under Solvent-Free Conditions, J. Braz. Chem. Soc., 19, p. 1595 (2008).

[21] Kiasat A.R.,  Fallah-Mehrjardi  M.,  Dowex  as Reusable Acidic Polymeric Catalyst in the Efficient and Regioselective Conversion of Epoxides into β-Hydroxy Thiocyanates under Solvent Free Conditions, J. Chin. Chem. Soc. 55, p. 1119 (2008).

[22] Kiasat  A.R.,  Zayadi  M.,  Polyethylene  Glycol Immobilized on Silica Gel as a New Solid-Liquid Phase-Transfer Catalyst for Regioselective Azidolysis of Epoxides in Water: An Efficient Route to 1,2-Azido Alcohols, Catal. Commun., 9, p. 2063 (2008).

[23] Nakagaki S., Castro K.A.D.F., Guilherme S.M., Matilte H., Sueli M.D., Fernando W., Catalytic Activity in Oxidation Reactions of Anionic Iron(III) Porphyrins Immobilized on Raw and Grafted Chrysotile, J. Braz. Chem. Soc., 17, p. 1672 (2006).

[24] Baverez, M., Bastick, J., Action Du Methanol Sur Les Gels De Silice, J. Bull. Soc. Chim. Fr., 12, p. 3662 (1965).

[25] Firouzabadi H., Iranpoor N., Karimi B., Hazarkhami H., Highly Efficient Transdithioacetalization of Acetals Catalyzed by Silica Chloride, Synlett, p. 263 (2000).