Synlett 2006(4): 0659-0660  
DOI: 10.1055/s-2006-932493
© Georg Thieme Verlag Stuttgart · New York


Yue-dong Lu*
Department of Applied Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China
Further Information

Publication History

Publication Date:
20 February 2006 (online)


(Diacetoxy)iodobenzene (DIB), one of the most signif- icant species among the family of hypervalent iodines, has been widely used as an effective oxidant in synthesis of various compounds, especially those containing hetero­atoms like N and O. According to the mechanism, the ­oxidation can be generally classified as either ionic-type or radical-type. In the latter, the oxidations are usually carried out in the presence of molecular iodine. Both can be utilized to prepare compounds through oxidative ring-opening or cyclic closure. DIB can also be applied to other types of reaction, such as electrophilic addition and ­bromination.


  • 1 Hernandez R. Leon EI. Moreno P. Riesco-Fagundo C. Suarez E. J. Org. Chem.  2004,  69:  8437 
  • 2 Togo H. Harada Y. Yokoyama M. J. Org. Chem.  2000,  65:  926 
  • 3 Francisco CG. Herrera AJ. Suarez E. J. Org. Chem.  2002,  67:  7439 
  • 4 Das B. Holla H. Mahender G. Banerjee J. Reddy MR. Tetrahedron Lett.  2004,  45:  7347 
  • 5 Mamaeva EA. Bakibaev AA. Tetrahedron  2003,  59:  7521 
  • 6 Boye AC. Meyer D. Ingison CK. French AN. Wirth T. Org. Lett.  2003,  5:  2157 
  • 7 Braddock DC. Cansell G. Hermitage SA. Synlett  2004,  461 
  • 8 Koposov AY. Boyarskikh VV. Zhdankin VV. Org. Lett.  2004,  6:  3613