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

Document Type : Research Paper


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



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.


[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.