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Synthesis 2008(22): 3675-3681  
DOI: 10.1055/s-0028-1083200
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Method for the Selective Iodination of α,β-Unsaturated Ketones

Zihua Wang, Guodong Yin, Jing Qin, Meng Gao, Liping Cao, Anxin Wu*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China
e-Mail: chwuax@mail.ccnu.edu.cn;
Further Information

Publication History

Received 4 July 2008
Publication Date:
23 October 2008 (online)

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Abstract

An efficient approach to α,β-unsaturated α′-iodo ketones directly from α,β-unsaturated ketones by selective iodination at the α′-position, without effect on the double bond and the activated benzene ring, in the presence of copper(II) oxide/iodine is described. The present method has the advantages of high yields, short reaction times, inexpensive reagents, mild reaction conditions, ease of manipulation, and the formation of cleaner products.

Key words

iodination - α,β-unsaturated ketones - α,β-unsaturated α′-iodo ketones - self-sorting

    References

  • 1a Kusama H. Onizawa Y. Iwasawa N. J. Am. Chem. Soc.  2006,  128:  16500 
    Google Scholar
  • 1b Babu KS. Li X.-C. Jacob MR. Zhang Q. Khan SI. Ferreira D. Clark AM. J. Med. Chem.  2006,  49:  7877 
    Google Scholar
  • 1c Li X.-C. Ferreira D. Jacob MR. Zhang Q. Khan SI. Elsohly HN. Nagle DG. Smillie TJ. Khan IA. Walker LA. Clark AM. J. Am. Chem. Soc.  2004,  126:  6872 
    Google Scholar
  • 2 Bora U. Saikia A. Boruah RC. Org. Lett.  2003,  5:  435 
    CrossrefGoogle Scholar
  • 3a Parker DL, Ratcliffe RW, Wilkening RR, and Wildonger KJ. inventors; WO  2001,082,923. 
  • 3b Rohrer SP. inventors; WO  2005,099,704. 
  • 3c Tsukano C. Siegel DR. Danishefsky SJ. Angew. Chem. Int. Ed.  2007,  46:  8840 
    Google Scholar
  • 4a Southwick PL. Pursglove LA. Numerof P. J. Am. Chem. Soc.  1950,  72:  1600 
    Google Scholar
  • 4b Southwick PL. Pursglove LA. Numerof P. J. Am. Chem. Soc.  1950,  72:  1604 
    Google Scholar
  • 4c Cristau H.-J. Torreilles E. Morand P. Christol H. Phosphorus, Sulfur Silicon Relat. Elem.  1985,  25:  357 
    Google Scholar
  • 5a Okamoto T. Kakinami T. Nishimura T. Hermawan I. Kajigaeshi S. Bull. Chem. Soc. Jpn.  1992,  65:  1731 
    Google Scholar
  • 5b Burluenga J. Marco-Arias M. González-Bobes F. Ballesteros A. González JM. Chem. Commun.  2004,  2616 
    Google Scholar
  • 6a Higgins SD. Thomas CB. J. Chem. Soc., Perkin Trans. 1  1982,  235 
    Google Scholar
  • 6b Bekaert A. Barberan O. Gervais M. Brion JD. Tetrahedron Lett.  2000,  41:  2903 
    Google Scholar
  • 6c Le Bras G. Provot O. Bekaert A. Peyrat J.-F. Alami M. Brion J.-D. Synthesis  2006,  1537 
    Google Scholar
  • 7 Horiuchi CA. Kiji S. Bull. Chem. Soc. Jpn.  1997,  70:  421 
    CrossrefGoogle Scholar
  • 8a Stavber S. Jereb M. Zupan M. Chem. Commun.  2002,  488 
    Google Scholar
  • 8b Pavlinac J. Stavber S. Zupan M. J. Org. Chem.  2006,  71:  1027 
    Google Scholar
  • 9a Rao MLN. Jadhav DN. Tetrahedron Lett.  2006,  47:  6883 
    Google Scholar
  • 9b Lee JC. Park JY. Yoon SY. Bae YH. Lee SJ. Tetrahedron Lett.  2004,  45:  191 
    Google Scholar
  • 9c Meshram HM. Reddy PN. Vishnu P. Sadashiv K. Yadav JS. Tetrahedron Lett.  2006,  47:  991 
    Google Scholar
  • 10 Kim JM. Na JE. Kim JN. Tetrahedron Lett.  2003,  44:  6317 
    CrossrefGoogle Scholar
  • 11 Johnson CR. Adams JP. Braun MP. Senanayake CBW. Wovkulich PM. Uskoković MR. Tetrahedron Lett.  1992,  33:  917 
    CrossrefGoogle Scholar
  • 12 Krafft ME. Cran JW. Synlett  2005,  1263 
    Article in Thieme ConnectGoogle Scholar
  • 13 Benhida R. Blanchard P. Fourrey J.-L. Tetrahedron Lett.  1998,  39:  6849 
    CrossrefGoogle Scholar
  • 14 Jereb M. Stavber S. Zupan M. Synthesis  2003,  853 
    Article in Thieme ConnectGoogle Scholar
  • 15 Whang JP. Yang SG. Kim YH. Chem. Commun.  1997,  1355 
    CrossrefGoogle Scholar
  • 16a Yin G. Zhou B. Meng X. Wu A. Pan Y. Org. Lett.  2006,  8:  2245 
    Google Scholar
  • 16b Yin G. Gao M. She N. Hu S. Wu A. Pan Y. Synthesis  2007,  3113 
    Google Scholar
  • 16c Yin G. Wang Z. Chen A. Wu A. Pan Y. J. Org. Chem.  2008,  73:  3377 
    Google Scholar
  • 17 Drake NL. Allen P. Org. Synth. Coll. Vol. I   John Wiley & Sons; London: 1941.  p.77 
    Google Scholar
  • 18a Kuo PC. Damu AG. Cherng CY. Jeng JF. Teng CM. Cheng ZJ. Lee EJ. Wu TS. Arch. Pharmacal Res.  2005,  28:  518 
    Google Scholar
  • 18b Kim DSHL. Kim JY. Bioorg. Med. Chem. Lett.  2004,  14:  1287 
    Google Scholar
  • 19a Buszek KR. Brown N. Org. Lett.  2007,  9:  707 
    Google Scholar
  • 19b Lin Y.-M. Li Z. Casarotto V. Ehrmantraut J. Nguyen AN. Tetrahedron Lett.  2007,  48:  5531 
    Google Scholar
  • 19c Peach P. Cross DJ. Kenny JA. Mann I. Houson I. Campbell L. Walsgrove T. Wills M. Tetrahedron  2006,  62:  1864 
    Google Scholar
  • 19d Peppe C. das Chagas RP. J. Organomet. Chem.  2006,  691:  5856 
    Google Scholar
  • 19e Paul S. Gupta M. Synth. Commun.  2005,  35:  213 
    Google Scholar
  • 19f Mitsudo T. Takagi M. Zhang S.-W. Watanabe Y. J. Organomet. Chem.  1992,  423:  405 
    Google Scholar
  • 20 Krishnamurty HG. Ghosh S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1986,  25:  411 
    Google Scholar
  • 21 Elias G. Roa MNA. Eur. J. Med. Chem.  1988,  23:  379 
    CrossrefGoogle Scholar
  • 22 Correa WH. Scott JL. Green Chem.  2001,  3:  296 
    CrossrefGoogle Scholar
  • 23 Tanikaga R. Konya N. Hamamura K. Kaji A. Bull. Chem. Soc. Jpn.  1988,  61:  3211 
    CrossrefGoogle Scholar
  • 24 Dos Santos AA. Castelani P. Bassora BK. Fogo JC. Costa CE. Comasseto JV. Tetrahedron  2005,  61:  9173 
    CrossrefGoogle Scholar
  • 25 Dodero VI. Koll LC. Belen Faraoni M. Mitchell TN. Podesta JC. J. Org. Chem.  2003,  68:  10087 
    CrossrefPubMedGoogle Scholar
  • 26a Cort AD. J. Org. Chem.  1991,  56:  6708 
    Google Scholar
  • 26b Baird WC. Surridge JH. J. Org. Chem.  1970,  35:  3436 
    Google Scholar