PDF icon Download PDF
Synthesis 2010(9): 1467-1472  
DOI: 10.1055/s-0029-1218698
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Ecofriendly Iodination of Activated Aromatics and Coumarins Using Potassium Iodide and Ammonium Peroxodisulfate

Nemai C. Ganguly*, Sujoy Kumar Barik, Sanjoy Dutta
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
Fax: +91(33)25828282; e-Mail: nemai_g@yahoo.co.in;
Further Information

Publication History

Received 19 January 2010
Publication Date:
12 March 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Corrected by:

Ecofriendly Iodination of Activated Aromatics and Coumarins Using Potassium Iodide and Ammonium PeroxodisulfateSynthesis 2011; 2011(05): 828-828
DOI: 10.1055/s-0030-1258441

Abstract

An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycoumarins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electron-rich C3, are some of the key advantageous features of the method.

Key words

iodination - potassium iodide - ammonium peroxodisulfate - activated aromatics - coumarins

    References

  • 1a Seevers RH. Counsell RE. Chem. Rev.  1982,  82:  575 
    Search in Google Scholar
  • 1b Levin RH. React. Intermed. (Wiley)  1985,  3:  1 
    Search in Google Scholar
  • 1c Merkushev EB. Synthesis  1988,  923 
  • 1d Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; New York: 1998. 
  • 1e Beletskaya IP. Cheprakov AV. Coord. Chem. Rev.  2004,  248:  2337 
    Search in Google Scholar
  • 1f Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev.  2002,  102:  1359 
    Search in Google Scholar
  • 2a Butler A. Walker JV. Chem. Rev.  1993,  93:  1937 
    Search in Google Scholar
  • 2b Sovak M. Radiocontrast Agents. Handbook of Experimental Pharmacology   Springer; Berlin: 1993. 
  • 3a Zubia E. Luis FR. Massanet GM. Collado IG. Tetrahedron  1992,  48:  4239 
    Search in Google Scholar
  • 3b Knobler RM. Hönigmann H. Edelson RL. In Psoralen DNA Photobiology   Vol. II:  Gasparro FP. CRC Press; Boca Raton: 1988.  p.117-134  
    Search in Google Scholar
  • 3c Parrish JA. Stern RS. Pathak MA. Fitzpatric TB. In Science of Photomedicine   Regan JD. Parrish JA. Plenum Press; New York: 1982.  p.595-624  
  • 4 Pescitelli G. Berova N. Xiao TL. Rozhkov VR. Larock RC. Armstrong DW. Org. Biomol. Chem.  2003,  1:  186 ; and references cited therein
    CrossrefSearch in Google Scholar
  • 5a Orito K. Hatakeyama T. Takeo M. Suginome H. Synthesis  1995,  1273 
  • 5b Krishna Mohan KVV. Narender N. Kulkarni SJ. Tetrahedron Lett.  2004,  45:  8015 
    Search in Google Scholar
  • 5c Sy WW. Tetrahedron Lett.  1993,  34:  6223 
    Search in Google Scholar
  • 5d Lulinski P. Skulski L. Bull. Chem. Soc. Jpn.  2000,  73:  951 
    Search in Google Scholar
  • 5e Sujuki H. Org. Synth. Coll. Vol. VI   John Wiley & Sons; London: 1988.  p.700 
  • 5f Lulinski P. Skulski L. Bull. Chem. Soc. Jpn.  1997,  70:  1665 
    Search in Google Scholar
  • 5g Krassowska-Swiebocka B. Lulinski P. Skulski L. Synthesis  1995,  926 
  • 5h Brazdil LC. Cutlar C. J. J. Org. Chem.  1996,  61:  9621 
    Search in Google Scholar
  • 5i Alexander VM. Khandekar AC. Samant SD. Synlett  2003,  1895 
  • 5j Cambie R. C. Rutledge P. S. Smith-Palmer T. Woodgate PD. J. Chem. Soc., Perkin Trans. 1  1976,  1161 
  • 6 Fristad WE. Peterson JR. Tetrahedron Lett.  1983,  24:  4547 
    CrossrefSearch in Google Scholar
  • 7 Gelbard G. Polymer-Supported Reagents, In Handbook of Green Chemistry and Technology   Clark JH. Macquarrie D. Blackwell Science; Oxford: 2002. 
  • 8 Clerici A. Porta O. Can. J. Chem.  1980,  58:  2117 
    CrossrefSearch in Google Scholar
  • 9a Lakouraj MM. Bahrami KJ. J. Chem. Res., Synop.  2002,  222 
  • 9b Minghu N. Guichun Y. Zuxing C. React. Funct. Polym.  2000,  44:  49 
    Search in Google Scholar
  • 9c Verma RS. Meshram HM. Tetrahedron Lett.  1997,  38:  7973 
    Search in Google Scholar
  • 10 Chen F.-E. Ling X.-H. He Y.-P. Peng X.-H. Synthesis  2001,  1772 
    Thieme Connect
  • 11 Ganguly NC. Datta M. Synlett  2004,  659 
    Thieme Connect
  • 12 Yang SG. Kim YH. Tetrahedron Lett.  1999,  40:  6051 
    CrossrefSearch in Google Scholar
  • 13 Hossain DMd. Oyamada J. Kitamura T. Synthesis  2008,  690 
    Thieme Connect
  • 14 Iskra J. Stavber S. Zupan M. Synthesis  2004,  1869 
    Thieme Connect
  • 15 Kajigaeshi S. Kakinami T. Yamasaki H. Fujisaki S. Kondo M. Okamoto T. Chem. Lett.  1987,  2109 
    Crossref
  • 16 Ghosal S. Dutta SK. Indian J. Chem.  1968,  6:  301 
    Search in Google Scholar
  • 17 Ganguly NC. De P. Dutta S. Synthesis  2005,  1103 
    Thieme Connect
  • 18a Dictionary of Organic Compounds   Buckingham J. 5th ed., Vol. III:  Chapman and Hall; New York: 1982. 
  • 18b Kometani T. Watt DS. J. Org. Chem.  1985,  50:  5384 
    Search in Google Scholar
  • 18c Kajigaeshi S. Kakinami T. Yamasaki H. Fujisaki S. Kondo M. Okamoto T. Chem. Lett.  1987,  2109