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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 23
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Original Articles

A Practical Iodination of Aromatic Compounds by Using Iodine and Iodic Acid

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Pages 3506-3513 | Received 19 Aug 2009, Published online: 05 Nov 2010

REFERENCES

  • Farina , V. In Comprehensive organometallic Chemistry II ; E.W. Abel , F.G.A. Stone , and G. Wilkinson (Eds.); Pergamen Press : Oxford , 1995 , vol. 12 , pp. 161 – 240 .
  • Diederich , F. ; Stang , P. J. Metal Catalysed Cross Coupling Reactions ; Wiley-VCH : Weinheim , Germany , 1988 .
  • (a) Larock , R. C. ; Lee , N. H. Efficient free radical and palladium catalysed tandem alkene insertion: a new approach to benzoprostacyclins . J. Org. Chem. 1991 , 56 , 6253 ; (b) Larock , R. C. ; Yum , E. K. Synthesis of indoles via palladium catalysed heteroannulation of internal alkynes . J. Am. Chem. Soc. 1991 , 113 , 6689 ; (c) Busacca , C. A. ; Johnson , R. E. Synthesis of novel tetrahydrobenzazepinones . Tetrahedron Lett. 1992 , 33 , 165 ; (d) Swenton , J. S. ; Callinan , A. ; Wang , S. Efficient synthesis of vinyl ethers of spiroquinol ketals and their high yield photochemical oxygen to carbon [1, 3]-shift to spiro-fused 2, 5-cycohexadienanes . J. Org. Chem. 1992 , 57 , 78 .
  • (a) Seevers , R. H. ; Counsell , R. E. Radioiodination of techniques for small organic molecules . Chem. Rev. 1982 , 82 , 574 ; (b) Nicolaou , K. C. The battle of calicheamicin g1 1 . Angew. Chem., Int. Ed. Engl. 1993 , 32 , 1377 .
  • Sovak , M. Radiocontrast agents; In Handbook of Experimental Pharmacology ; Springer : Berlin , 1993 .
  • Seevers , R. H. ; Counsell , R. E. Radioiodination of techniques for small organic molecules . Chem. Rev. 1982 , 82 , 575 .
  • (a) Heindel , N. D. ; Burnes , H. D. ; Honds , T. ; Brandy , L. W. , Eds.; Chemistry of Radiopharmaceuticals ; Masson : New York , 1997 ; (b) Nicolaou, K. C. The battle of calicheamicin g1 1. Angew. Chem., Int. Ed. Engl. 1993, 32, 1377.
  • Noda , Y. ; Kashima , M. An efficient and regioselective direct iodination using iodine and nitrogen dioxide . Tetrahedron Lett. 1997 , 38 , 6225 – 6228 .
  • Zupan , M. ; Iskra , J. ; Stavber , S. Mild and regioselective iodination of electron rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid . Tetahedron Lett. 1997 , 38 , 6305 – 6306 .
  • Carreno , M. C. ; Ruano , J. G. ; Sanz , G. ; Toledo , M. A. ; Urbano , A. Mild and regioselective iodination methoxybenzenes and napthalenes with N-iodosuccinimide . Tetrahedron Lett. 1996 , 37 , 4081 – 4084 .
  • Akhlaghinia , B. ; Rahmani , M. Mild and Efficient Iodination of aromatic compounds with Trichloroisocyanuric Acid/I2/Wet SiO2 System. J. Turk. Chem. 2009, 31,1–6.
  • Orito , K. ; Hatakeyama , T. ; Takeo , M. Iodination of alkyl aryl ethers by mercury II) oxide—iodine reagent in dichloroethane . Synthesis 1995 , 1273 – 1277 .
  • Hubig , S. M. ; Jung , W. ; Kochi , J. K. Cation radical as intermediates in aromatic halogenation with iodine monochloride: Solvent and salt effect on the competition between chlorination and iodination . J. Org. Chem. 1994 , 59 , 6233 – 6244 .
  • Barluenga , J. ; Gonzalez , J. M. ; Garcia-Martin , M. A. ; Campos , P. J. ; Asensia , G. Acid mediated reaction of bis (pyridine) iodonoum (I) tetrafluoroborate witharomatic compounds: A selective and general iodination method . J. Org. Chem. 1993 , 58 , 2058 – 2060 .
  • Olah , G. A. ; Wang , D. ; Sandford , G. ; Prakash , G. K. S. Synthetic methods and reagents, 181. Iodination of deactivated aromatics with N-iodosuccinimide in trifluromethanne sulphonic acid (NIS-CF3SO3H) via in situ generated superelectrophilic iodine (I) trifluromethannesulphonate . J. Org. Chem. 1993 , 58 , 3194 – 3195 .
  • Sy , W. W. Iodination of methoxyamphetamines with iodine and silver sulphate . Tetrahedron Lett. 1993 , 34 , 6223 – 6224 .
  • Bachki , A. ; Foubelo , F. ; Yus , M. Aromatic iodination with the I2-HgX2 combination . Tetrahedron 1994 , 50 , 5139 – 5146 .
  • Edgar , K. J. ; Falling , S. N. An efficient and selective method for preparation ofiodophenol . J. Org. Chem. 1990 , 55 , 5287 – 5291 .
  • Patil , B. R. ; Bhusare , S. R. ; Pawar , R. P. ; Vibhute , Y. B. Iodine and iodic acid: an efficient reagent for iodination of aryl hyderoxy ketones . Tetrahedron Lett. 2005 , 46 , 7179 – 7181 .
  • Patil , B. R. ; Bhusare , S. R. ; Pawar , R. P. ; Vibhute , Y. B. Regioselective iodination of hydroxylated aromatic ketones . Arkivoc 2006 , 1 , 104 – 108 .
  • Khansole , S. V. ; Junne , S. B. ; Sayyed , M. A. ; Vibhute , Y. B. Convenient and efficient method for iodination of aromatic amines by pyridinium iodochloride . Synth. Commun. 2008 , 38 , 1792 – 1798 .
  • Aldrich Chemical Company . Handbook of Fine Chemicals ; Aldrich Chemical Company : Bangalore , India , 2007–2008 .
  • Khansole , S.V. ; Mokle , S.S. ; Sayyed , M.A. ; Vibhute , Y.B. PyridiniumIodochloride: An efficient reagent for iodination of hydroxylated aromatic ketones and aldehydes . J. Chin. Chem. Soc. 2008 , 55 , 871 – 874 .
  • Sayyed , M. A. ; Junne , S. B. ; Vibhute , A. Y. ; Vibhute , Y. B. An improved protocol for synthesis of iodohydroxy benzaldehyde using iodine and iodic acid . Int. J. Chem. Soc. 2008 , 6 , 192 – 196 .
  • Vibhute , A. Y. Studies on synthesis and biological activity of some new heterocyclic compounds . Thesis submitted to swami Ramanand Teerth Marathwada University , Nanded (M.S.), 2008 , India .

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