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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;
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Publication History

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

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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

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