Hypervalent iodine catalyzed Hofmann rearrangement of amides has  been studied with Oxone (4 eq) as the terminal oxidant and iodoarene  (10%) as the pre-catalyst in acetic acid/water/H2SO4 (6:10:1) at 40 oC  for 4h.  Among the aryl iodides tested, 2-tert-butyliodobenzene gave  the best results.  While electron-rich, 2-substituted benzamides reacted  well, other amides were very sluggish under these conditions.  Further  study on the scope and limitations of this reaction is underway.

2-tert-Butyliodobenzene: A pre-catalyst for Hofmann rearrangement of electron-rich, 2-substituted benzamides via in situ generated hypervalent iodine species

244th National Meeting (2012)

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