Solvent-Free Synthesis of Aryl Iodide Using Nano SiO2/HIO4 as a Reusable Acid Catalyst

Document Type: Research Paper

Authors

1 Departement of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan,I.R. Iran.

2 School of Chemistry, Damghan University, Damghan ,I.R. Iran

10.7508/jns.2014.03.008

Abstract

An efficient and environmentally benign   method for the synthesis of aryl iodides have been developed by diazotization of aromatic amines with NaNO2 and nanosilica periodic acid (nano-SPIA) as a green catalyst via grinding followed by a sandmeyer iodination by KI under solvent-free conditions at room temperature. The ensuing aryl diazonium salts supported on nano-SPIA were sufficiently stable to be kept at room temperature in the dry state. This method is a novel, efficient, eco-friendly route for solvent-free synthesis of aryl iodides.

Keywords


[1] S.C.  Dickerman, D.J. Desouza and N. J. Jacobson, J. Org. Chem., 34 (1969) 710-713.

[2] E.V. Merkushev, Russ. Chem. Rev., 53 (1984) 343-350.

[3] A. Hubbard, T. Okazaki  and  K.K. Laali, J.  Org. Chem. 73 (2008) 316-319.

[4] J.K. Kochi, J. Am. Chem. Soc., 79 (1957) 2942-2948.

[5] H.H. Hodgson, Chem. Rev., 40 (1947)  251-277.

[6] N. Bicak and H. Bulbul,  Polymer Bull., 46 (2001) 139-145.

[7] W.B. Smith and O.C. Ho, J. Org. Chem., 55 (1990)  2543-2545.

[8] V. Nair and S.G. Richardson, Synthesis 8 (1982) 670-672.

[9] J.I.G. Cadogan, D.A. Roy and D.M. Smith, J. Chem. Soc., 95 (1966) 1249-1250.

[10] W. Baik, W. Luan, H.J. Lee, C.H. Yoon, S. Koo and B.H. Kim, Can. J. Chem., 83 (2005) 213-219.

[11] M. Barbero, I. Degani, S. Dughera and R. Fochi, J. Org. Chem., 64 (1999) 3448-3453.

[12] A.D. Towns, Dyes and Pigments 42 (1999) 3-28.

[13] M.E. Moon, Y. Choi, Y. Min Lee, V. Vajpayee, M. Trusova and V.D. Filimonov, Tetrahedron Lett., 51 (2010) 6769-6771.

[14] A.  Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili and A. Najafi Chermahini Dyes and Pigments 81 (2009) 240-244.

[15] D.A. Gorlushk, D.V. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Gob, H.Y. Hwang, E.H. Cha and K. Chi, Tetrahedron Lett., 49 (2008) 1080–1082.

 [16] (a) A. R. Pourali, M. Ghanei, Bull Korean Chem. Soc. 27 (2006) 1674-1676. (b) A. R. Pourali, Mendelev Commun. 20 (2010) 113-115. (c) A. Bamoniri, A. Ghorbani-Choghamarani,  B. F. Mirjalili, Phosphorus, Sulfur, and Silicon and the Related Elements. 186 (2001) 381-388.  (d)  M. A. Zolfigol, B. F. Mirjalili, A. Bamoniri, M. A. Karimi  , A. Zarei, L. Khazdooz, Bull Korean Chem. Soc., 25 (2004) 1414–1416.

[17] Weast, R C.  CRC Handbook of Chemistry and Physics. (1968). 67th Ed, CRC Press: Boca Raton, FL, USA.