Oxidative Iodination of Aromatic Amides Using Sodium Perborate or Hydrogen Peroxide with Sodium Tungstate†

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Philipp Beinker, James R. Hanson, Nadja Meindl and Inmaculada C. Rodriguez Medina


Abstract

Hydrogen peroxide or sodium perborate in the presence of a sodium tungstate catalyst are shown to be cheap oxidants for the iodination of aromatic amides using potassium iodide as the source of the iodine.


References

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