Skip to main content
SpringerLink
Log in

A mild and highly chemoselective iodination of alcohol using polymer supported DMAP

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

The synthesis of organic compounds using polymer supported catalysts and reagents, where the required product is always in solution, has been of great interest in recent years, both in industries and academia especially in pharmaceutical research. Here, a simple and efficient method for conversion of alcohols into their iodides in high yield using polymer supported 4-(Dimethylamino)pyridine (DMAP) is described. Polymer supported DMAP is used in catalytic amount and is recovered and reused several times. Additionally, this method is highly chemoselective.

A mild and highly selective iodination of alcohols using polymer supported 4-(Dimethylamino)pyridine (DMAP) in catalytic amount is reported. The base catalyst can be easily recovered by simple filtration and reused several times without appreciable loss in activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

References

  1. (a) Frisch A C and Beller M 2005 Angew. Chem. Int. Ed. 44 674; (b) Su M D and Chu S Y 1999 J. Am. Chem. Soc. 121 1045

  2. Naso F and Marchese G 1983 In Carbon–carbon bond formation involving organic halides and transition metal compounds. The Chemistry halides, pseudo-halides and azides S Patai and Z J Rappoport (Eds.) (New York: Wiley) p.1353

  3. Abraham G E and Flechas J E 2007 The Original Internist 15 8

    Google Scholar 

  4. Arroyo-Helguera O, Rojas E, Delgado G and Aceves C 2008 Endocr. Relat. Cancer 15 1003

    Article  CAS  PubMed  Google Scholar 

  5. Hajipour A R, Mostafavi M and Ruoho A E 2009 Org. Prep. Proced. Int. 41 87

    Article  CAS  Google Scholar 

  6. Jung M E and Ornstein P L 1977 Tetrahedron. Lett. 31 2659

    Article  Google Scholar 

  7. Martinez A G, Alvarez R M, Vilar E T, Fraile A G, Barnica J O, Hanack M and Subramanian L R 1987 Tetrahedron Lett. 28 6441

    Article  Google Scholar 

  8. Firouzabadi H, Iranpoor N and Jafarpour M 2004 Tetrahedron Lett. 45 7451

    Article  CAS  Google Scholar 

  9. Hayat S, Atta-ur-Rahman, Khan K M, Choudhary M I, Maharvi G M, Zia-Ullah and Bayer E 2003 Synth. Commun. 33 2531

    Article  CAS  Google Scholar 

  10. Firouzabadi H, Iranpoor N and Ebrahimzadeh F 2006 Tetrahedron Lett. 47 1171

    Google Scholar 

  11. Hajipour A R, Falahati A R and Ruoho A E 2006 Tetrahedron Lett. 47 4191

    Article  CAS  Google Scholar 

  12. (a) Garegg P J and Samuelsson G J 1979 J. Chem. Soc., Chem. Commun. 978; (b) Garegg P J, Johansson R, Ortega C and Samuelsson G J 1982 Chem. Soc., Chem. commun. 978; (b) Garegg P J, Johansson R, Ortega C and Samuelsson G J 1982 Chem. Soc., Perkin Trans. 1 681

  13. Tundo P and Venturello P 1979 Synthesis 12 952

    Article  Google Scholar 

  14. (a) Anilkumar G, Nambu H and Kita Y 2002 Org. Proc. Res. Dev. 6 190; (b) Rokhum SL, Vanlalveni C and Lalfakzuala R 2013 IJETCAS 13 370

  15. Appel R 1975 Angew. Chem. Int. Ed. Engl. 14 801

    Article  Google Scholar 

  16. (a) Hodge P 2005 Ind. Eng. Chem. Res. 44 8542; (b) Gladysz J A 2002 Chem. Rev. 103 3216; (c) McNamara C A, Dixon M J and Bradley M 2002 Chem. Rev. 102 3275; (d) Sandaroos R, Goldani M T, Damavandi S and Mohammadi A 2012 J. Chem. Sci. 124 871; (e) Islam N S and Boruah J J 2015 J. Chem. Sci. 127 777

  17. (a) Pathak G and Rokhum SL 2015 ACS Comb. Sci. 17 483; (b) Rokhum SL and Bez 2013 Can. J. Chem. 91 300; (c) Rokhum SL and Bez G 2013 Tetrahedron Lett. 54 5500; (d) Rokhum SL and Bez G 2011 J. Chem. Sci. 124 687; (e) Bora P P, Vanlaldinpuia K, Rokhum SL and Bez G 2011 Synth. Commun. 41 2674; (f) Rokhum SL and Bez G 2011 Synth. Commun. 41 548; (g) Vanlaldinpuia K, Sema H A, Rokhum SL and Bez G 2010 Chem. Lett. 39 228; (h) Das D, Chanda T and Rokhum SL 2015 Acta Chim. Slov. 62 775

Download references

Acknowledgements

We gratefully acknowledge Science and Engineering Research Board (SERB)-DST, Govt. of India, New Delhi for financial supports [sanctioned no: SB/FT/CS-103/2013, SB/EMEQ-076/2014].

Author information

Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Silchar, Assam, 788 010, India

    DIPARJUN DAS & SAMUEL LALTHAZUALA ROKHUM

  2. Department of Chemistry, North Eastern Hill University, Shillong, Meghalaya, 793 022, India

    JASHA MOMO H ANAL

Authors
  1. DIPARJUN DAS
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. JASHA MOMO H ANAL
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. SAMUEL LALTHAZUALA ROKHUM
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to SAMUEL LALTHAZUALA ROKHUM.

Additional information

Supporting information (SI)

Spectral data (1H NMR and 13C NMR) are available as Supplementary Information at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOCX 983 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

DAS, D., H ANAL, J.M. & ROKHUM, S.L. A mild and highly chemoselective iodination of alcohol using polymer supported DMAP. J Chem Sci 128, 1695–1701 (2016). https://doi.org/10.1007/s12039-016-1158-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-016-1158-1

Keywords

Search

Navigation