Synlett 2011(3): 432-433  
DOI: 10.1055/s-0030-1259315
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Iodobenzene Diacetate - Efficient Terminal Oxidant for Transition-Metal-Mediated Transformations

Ioana Dumitru*
University of Bucharest, Department of Chemistry, Division of ­Organic Chemistry, 90-92 Panduri Street, District 5, Bucharest, ­Romania
e-Mail: ioanaa.dumitru@gmail.com;
Further Information

Publication History

Publication Date:
25 January 2011 (online)

Introduction

The most important use of hypervalent iodine compounds is as oxidizing agents replacing many other toxic reagents, usually based on heavy metals. Also, it has been observed that the synthetic properties of trivalent iodine compounds are often similar to those of lead and thallium derivatives, somehow with better yields and improved toxicity. The iodobenzene diacetate (most used acronyms are DIB or PIDA), a trivalent iodine derivative, which presents itself as white crystalline powder, is a prominent member. It has found multiple applications in organic chemistry as efficient and inexpensive reagent. [¹] Recently, its ability to act as terminal oxidant in palladium-, gold- or copper-­mediated transformations was disclosed and subsequently demonstrated. DIB is commercially available and can also be easily prepared by oxidation of iodobenzene with hydrogen peroxide urea complex in the presence of acetic anhydride, [²a] peracetic acid, [²b] or sodium perborate [¹a] (Scheme  [¹] ).

Scheme 1

    References

  • 1a Zhdankin VV. Arkivoc  2009,  (i):  1 
  • 1b Zhdankin VV. Stang PJ. Chem Rev.  2008,  108:  5299; and references cited therein 
  • 2a Sharefkin JG. Saltzman H. Org. Synth., Coll. Vol. V  1973,  660 
  • 2b Page TK. Wirth T. Synthesis  2006,  3153 
  • 3 Yan J. Lin F. Yang Z. Synthesis  2007,  1301 
  • 4 Yan J. Li J. Cheng D. Synlett  2007,  2442 
  • 5 Rodriguez A. Moran WJ. Eur. J. Org. Chem.  2009,  1313 
  • 6 Kalyani D. Sanford MS. Org. Lett.  2005,  7:  4149 
  • 7 Dick AR. Hull KH. Sanford MS. J. Am. Chem. Soc.  2004,  126:  2300 
  • 8 Streuff J. Hovelmann CH. Nieger M. Muiz K. J. Am. Chem. Soc.  2005,  127:  14586 
  • 9 Desai LV. Hull KH. Sanford MS. J. Am. Chem. Soc.  2004,  126:  9542 
  • 10 Liu G. Stahl SS. J. Am. Chem. Soc.  2006,  128:  7179 
  • 11a Li Y. Song D. Dong VM. J. Am. Chem. Soc.  2008,  130:  2962 
  • 11b Wang W. Wang F. Shi M. Organometallics  2010,  29:  928