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

(Diacetoxy)iodobenzene

Yue-dong Lu*
Department of Applied Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. of China
e-Mail: luyuedong@sina.com;

Further Information

Publication History

Publication Date:
20 February 2006 (online)

Biographical Sketches

Yue-dong Lu was born in 1981 at Dongyang, Zhejiang Province (P. R. of China). He obtained his Bachelor of Science from Zhejiang Sci-Tech University. Presently he is working as a postgraduate in the same university under the supervision of Professor Min Xia. His research is focused on synthetic methodology in the field of organic chemistry.

Introduction

(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.

Preparation

Properties

Abstracts

(A) Highly functionalized nitriles have been synthesized by an alkoxy radical fragmentation of cyclic β-hydroxy azides under mild conditions with DIB and iodine. [1]

(B) A new preparative method for 3,4-dihydro-2,1-benzothiazine 2,2-dioxides from N-alkyl 2-(aryl)ethanesulfonamides with DIB and iodine under photochemical conditions has been described. [2]

(C) The reaction of specifically protected anhydroalditols with DIB and iodine is a mild and selective procedure for the synthesis of chiral 2,7-dioxabicyclo[2.2.1]heptane ring systems under ­neutral conditions. [3]

(D) Treatment of aldoximes with activated alkenes in the presence of DIB afforded isoxazolines smoothly in high yields and under very mild conditions. [4]

(E) Mamaeva et al. reported the first example that 1,2,4-thia­diazoles derivatives could be obtained in good to excellent yield by the oxidation of 1-monosubstituted thioureas with DIB. [5]

(F) A novel lactonization of 4-arylpent-4-enoic acids is described using DIB for the electrophilic addition onto a double bond. The hypervalent iodine species acts as a hypernucleofuge, generating intermediate phenonium ions, which react to form aryl-migrated lactones. [6]

(G) Mild bromination of olefins and activated arenes can be carried out in situ by the generation of ‘Br+’ using DIB and LiBr. [7]

(H) Some new amino acid-derived iodobenzene dicarboxylates have been prepared by the reaction of DIB with N-protected ­natural amino acids through ligand exchange. These compounds in the presence of iodide anion can be used as reagents for β-iodo­carboxylation of alkenes leading to the respective amino acid ­esters. [8]

    References

  • 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 

    References

  • 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