National Academy Science Letters

, Volume 38, Issue 1, pp 45–48 | Cite as

Direct Iodination of Aromatic Compounds by Using Polymer-Supported Dichloroiodate as an Efficient Reagent under Mild Conditions

  • Sepideh Bahrami-Nasab
  • Ali Reza Pourali
  • S. Mohamad Reza Nazifi
Research Article
First Online:
Received:
Revised:
Accepted:

Abstract

A new polymeric reagent was prepared by supporting dichloroiodate on poly (1,4-phenylene-2,5-pyridine dicarboxylamide). This polymeric reagent was used for the direct iodination of arenes under mild aprotic conditions.

Keywords

Iodination Polymer supported Aprotic conditions Dichloroiodate 
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Notes

Acknowledgments

We gratefully acknowledge the financial support from the Research Council of Damghan University, Iran.

References

  1. 1.
    Khalilzadeh MA, Hosseini A, Shokrollahzadeh M, Halvagar M, Tajbakhsh M (2006) HIO4/Al2O3 as a new system for iodination of activated aromatics and 1,3-dicarbonyl compounds. Tetrahedron Lett 47:352–3228CrossRefGoogle Scholar
  2. 2.
    Firouzabadi H, Iranpoor N, Shiri M (2003) Direct and regioselective iodination and bromination of benzene, naphthalene and other activated aromatic compounds using iodine and bromine or their sodium salt in the presence of the iodine and bromine or their sodium salt in the presence of the Fe(NO3)3. 1.5 N2O4/charcoal system. Tetrahedron Lett 44:8781–8785CrossRefGoogle Scholar
  3. 3.
    Rodringuez-Franco MI, Dorronsoro I, Hernandez-Higueras AI, Atequera G (2001) A mild and efficient method for the regioselective iodination of pyrazoles. Tetrahedron Lett 42:863–865CrossRefGoogle Scholar
  4. 4.
    Adimurthy S, Raachandraiah G, Ghosh PK, Bedekrar AV (2003) A new, environment friendly protocol for iodination of electron-rich aromatic compounds. Tetrahedron Lett 44:5099–5101CrossRefGoogle Scholar
  5. 5.
    Bhilare SV, Deorukhkar AR, Darvatkar NB, Salunkhe MM (2008) Regioselective Iodination of Arenes Using Iodine/NaBO3·4H2O System in Ionic Liquid. Synth Commun 38:2881–2888CrossRefGoogle Scholar
  6. 6.
    Quintin J, Lewin G (2004) Regioselective 6-iodination of 5,6-dioxygenated flavones by benzyltriethylammonium dichloroiodate. Tetrahedron Lett 45:3635–3638CrossRefGoogle Scholar
  7. 7.
    Noda Y, Kashima M (1997) An efficient and regioselective direct iodination using iodine and nitrogen dioxide. Tetrahedron Lett 38:6225–6228CrossRefGoogle Scholar
  8. 8.
    Seung Gak Y, Yong Hae KA (1999) Practical iodination of aromatic compounds using tetrabutylammonium peroxydisulfate and iodine. Tetrahedron Lett 40:6051–6054CrossRefGoogle Scholar
  9. 9.
    Carman Careno M, Garcia Ruano JL, Sanz G, Toledo A, Urbano A (1996) Mild and regiospecific nuclear iodination of methoxybenzenes and naphthalenes with N-iodosuccinimide in acetonitrile. Tetrahedron Lett 37:4081–4084CrossRefGoogle Scholar
  10. 10.
    Arotsky J, Butler R, Darby AC (1966) Iodination of aromatic compounds with iodine in 20% oleum. Chem Commun 18:650–651Google Scholar
  11. 11.
    Tamami B, Borujeni KP (2009) Poly(vinylpyridine) supported reagents a review. Iran Polym J 18:191–206Google Scholar
  12. 12.
    Sumin Mitra S, Sreekumar K (1997) Polymer-bound benzyltriethylammonium polyhalides: recyclable reagent for the selective iodination of amines and phenols. React Funct Polym 32:281–291CrossRefGoogle Scholar
  13. 13.
    Pourali AR, Ghanei M (2006) Direct iodination of aromatic compounds with polyvinylpyrrolidone supported hydrogen peroxide (PVP-H2O2) and potassium iodide or molecular iodine. Chin J Chem 24:1077–1079CrossRefGoogle Scholar
  14. 14.
    Pourali AR, Khohdaragh R (2013) Iodination of organic compounds using anion exchange resin supported peroxodisulfate under mild aporotic conditions. Elixir Org Chem 57:13986–13990Google Scholar
  15. 15.
    Zakavi S, Abasi A, Pourali AR, Talebzadeh S (2012) Metalloporphyrin-catalyzed chemoselective oxidation of sulfides with polyvinylpyrrolidone-supported hydrogen peroxide: a simple catalytic system for selective oxidation of sulfides to sulfoxides. Bull Korean Chem Soc 33:35–38CrossRefGoogle Scholar
  16. 16.
    Zakavi S, Abasi A, Pourali AR, Rayati S (2008) Mn-porphyrin catalyzed epoxidation of alkenes with polyvinylpyrrolidone-supported H2O2. Bull Korean Chem Soc 29:866–868CrossRefGoogle Scholar
  17. 17.
    Pourali AR, Tabaean M, Nazifi SMR (2012) A novel and selective oxidation of benzylic alcohols with polymer-supported periodic acid under mild aprotic conditions. Chin Chem Lett 23:21–24CrossRefGoogle Scholar
  18. 18.
    Pourali AR (2010) Polymer-supported Oxone and tert-butyl hydroperoxide: new reagents for the epoxidation of α, β-unsaturated aldehydes and ketones. Mendeleev Commun 20:113–115CrossRefGoogle Scholar
  19. 19.
    Iranpoor N, Firouzabadi H, Pourali AR (2003) Selective N-Nitrosation of amines, N-alkylamides and N-alkylureas by N2O4 supported on cross-linked polyvinylpyrrolidone (PVP-N2O4). Synthesis 10:1591–1597CrossRefGoogle Scholar
  20. 20.
    Hajipour AR, Arbabian M, Ruoho E (2002) Tetramethylammonium dichloroiodate: an efficient and environmentally friendly iodination reagent for iodination of aromatic compound under mild and solvent-free conditions. J Org Chem 67:8622–8624CrossRefGoogle Scholar
  21. 21.
    Sathiyapriya R, Karunakaran RJ (2006) Iodination of alkylbenzenes using benzyltriphenylphosphonium dichromate/I2 system. E-J Chem 6:1164–1166CrossRefGoogle Scholar
  22. 22.
    Kajgiaesh S, Kakinami T, Morivaki M, Fujisaki S, Okamoto T (1989) Halogenation using quaternary ammonium polyhalides. aromatic bromination and iodination of arenes by use of benzyltrimethylammonium polyhalides-zinc chloride system. Bull Chem Soc Jpn 62:439–443CrossRefGoogle Scholar

Copyright information

© The National Academy of Sciences, India 2014

Authors and Affiliations

  • Sepideh Bahrami-Nasab
    • 1
  • Ali Reza Pourali
    • 1
  • S. Mohamad Reza Nazifi
    • 2
  1. 1.School of ChemistryDamghan UniversityDamghanIran
  2. 2.Department of Medicinal Chemistry, School of PharmacyIsfahan University of medical SciencesIsfahanIran

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