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Synthesis 2010(22): 3879-3882  
DOI: 10.1055/s-0030-1258250
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regiospecific Azidoiodination of Alkenes with Sodium Periodate, Potassium Iodide, and Sodium Azide: A High-Yield Synthesis of β-Iodoazides

Pandurang V. Chouthaiwale, Pratibha U. Karabal, Gurunath Suryavanshi, Arumugam Sudalai*
Chemical Engineering and Process Development Division, National Chemical Laboratory, Pashan Road, Pune 411 008, India
Fax: +91(20)25902676; e-Mail: a.sudalai@ncl.res.in;
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Publikationsverlauf

Received 19 July 2010
Publikationsdatum:
14. September 2010 (online)

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Abstract

The combination of sodium periodate, potassium iodide, and sodium azide has been found to be an efficient, simple, and inexpensive reagent system for azidoiodination of alkenes. The regiospecific 1,2-azidoiodination proceeds in an anti-Markovnikov fashion to produce β-iodoazides in excellent yields.

Key words

azides - alkenes - azidoiodination - β-iodoazides - regio­specific

    References

  • 1 Hassner A. Fowler FW. J. Org. Chem.  1968,  33:  2686 
    CrossrefGoogle Scholar
  • 2 Wasserman HH. Brunner RK. Buynak JD. Carter CG. Oku T. Robinson RP. J. Am. Chem. Soc.  1985,  107:  519 
    CrossrefGoogle Scholar
  • 3a Van Ende D. Krief A. Angew. Chem., Int. Ed. Engl.  1974,  13:  279 
    Google Scholar
  • 3b Denis JN. Krief A. Tetrahedron  1979,  35:  2901 
    Google Scholar
  • 4a Ranganathan S. Ranganathan D. Mehrotra AK. Tetrahedron Lett.  1973,  2265 
    Google Scholar
  • 4b Moorthy SN. Devaprabhakara D. Tetrahedron Lett.  1975,  257 
    Google Scholar
  • 5a Gallardo H. Conte G. Bryk F. Cristina M. Lourenco S. Costa MS. Ferreira VF. J. Braz. Chem. Soc.  2007,  18:  1285 
    Google Scholar
  • 5b Aufort M. Herscovici J. Bouhours P. Moreau N. Girard C. Bioorg. Med. Chem. Lett.  2008,  18:  1195 
    Google Scholar
  • 5c Tullis JS. VanRens JC. Natchus MG. Clark MP. De B. Hsieh LC. Janusz MJ. Bioorg. Med. Chem. Lett.  2003,  13:  1665 
    Google Scholar
  • 5d Lee T. Cho M. Ko S.-Y. Youn H.-J. Baek DJ. Cho W.-J. Kang C.-Y. Kim S. J. Med. Chem.  2007,  50:  585 
    Google Scholar
  • 5e Whiting M. Tripp JC. Lin Y.-C. Lindstrom W. Olson AJ. Elder JH. Sharpless KB. Fokin VV. J. Med. Chem.  2006,  49:  7697 
    Google Scholar
  • 6a Hantzsch A. Schumann M. Ber. Dtsch. Chem. Ges.  1900,  33:  522 
    Google Scholar
  • 6b Hassner A. Levy L. J. Am. Chem. Soc.  1965,  87:  4203 
    Google Scholar
  • 6c Hassner A. Acc. Chem. Res.  1971,  4:  9 
    Google Scholar
  • 7a Woodgate PD. Lee HH. Rutledge PS. Cambie RC. Synthesis  1977,  462 
    Google Scholar
  • 7b Terent’ev AO. Krylov IB. Kokorekin VA. Nikishin GI. Synth. Commun.  2008,  38:  3797 
    Google Scholar
  • 8 Barluenga J. Alvarez-Perez M. Fananas FJ. Gonzalez JM. Adv. Synth. Catal.  2001,  343:  335 
    CrossrefGoogle Scholar
  • 9a Kirschning A. Hashem MA. Monenschein H. Rose L. Schoning K.-U. J. Org. Chem.  1999,  64:  6522 
    Google Scholar
  • 9b Kirschning A. Monenschein H. Schmeck C. Angew. Chem. Int. Ed.  1999,  38:  2594 
    Google Scholar
  • 10 Nair V. George TG. Sheeba V. Augustine A. Balagopal L. Nair LG. Synlett  2000,  1597 
    Artikel in Thieme ConnectGoogle Scholar
  • 11 Curini M. Epifano F. Marcotullio MC. Rosati O. Tetrahedron Lett.  2002,  43:  1201 
    CrossrefGoogle Scholar
  • 12 Emmanuvel L. Shukla RK. Sudalai A. Suryavanshi G. Sivaram S. Tetrahedron Lett.  2006,  47:  4793 
    CrossrefGoogle Scholar
  • 13 Dewkar GK. Narina SV. Sudalai A. Org. Lett.  2003,  5:  4501 
    CrossrefPubMedGoogle Scholar
  • 14a Shaikh TM. Sudalai A. Tetrahedron Lett.  2005,  46:  5587 
    Google Scholar
  • 14b Chouthaiwale PV. Suryavanshi G. Sudalai A. Tetrahedron Lett.  2008,  49:  6401 
    Google Scholar
  • 15 Cambie RC. Hayward RC. Rutledge PS. Smith-Plalmer T. Swelland BE. Woodgate PD. J. Chem. Soc., Perkin Trans. 1  1979,  180 
    CrossrefGoogle Scholar
  • 16a L’abbe G. Hassner A. Angew. Chem., Int. Ed. Engl.  1971,  10:  98 
    Google Scholar
  • 16b Workentin MS. Wagner BD. Lusztyk J. Wayner DDM. J. Am. Chem. Soc.  1995,  117:  119 
    Google Scholar
  • 17a Tingoli M. Tiecco M. Chianelli D. Balducci R. Temperini A. J. Org. Chem.  1991,  56:  6809 
    Google Scholar
  • 17b Fontana F. Minisci F. Yan YM. Zhao L. Tetrahedron Lett.  1993,  34:  2517 
    Google Scholar
  • 18 Barluenga J. Campos-Gomez E. Rodriguez D. Gonzalez-Bobes F. Gonzalez JM. Angew. Chem. Int. Ed.  2005,  44:  5851 
    CrossrefGoogle Scholar
  • 19 Marinescu LG. Pedersen CM. Bols M. Tetrahedron  2005,  61:  123 
    CrossrefGoogle Scholar