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

  作者 GANGULY NEMAI C; BARIK SUJOY KUMAR; DUTTA SANJOY  
  选自 期刊  Synthesis;  卷期  2010年-9;  页码  1467-1472  
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[摘要]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.

 
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