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Synthesis 2009(24): 4183-4189  
DOI: 10.1055/s-0029-1217037
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed Sulfenylation of Indoles with Disulfides Promoted by a Catalytic Amount of Iodine

Xiao-Li Fang, Ri-Yuan Tang, Ping Zhong, Jin-Heng Li*
College of Chemistry and Materials Science, Wenzhou University, Wenzhou 325035, P. R. of China
Fax: +86(731)8872101; e-Mail: jhli@hunnu.edu.cn;
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Publication History

Received 24 June 2009
Publication Date:
12 October 2009 (online)

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Abstract

Selective sulfenylation of indoles with disulfides using iron(III) fluoride combined with iodine has been developed for the synthesis of sulfenylindoles. In the presence of iron(III) fluoride and iodine, a variety of disulfides underwent the reaction with indoles selectively to afford the corresponding sulfenylindoles in good to excellent yields. Moreover, reactions of indoles with 1,2-diphenyldiselane were also conducted under the same conditions, which smoothly afforded 3-selenylindoles in good yields.

Key words

iron(III) fluoride - sulfenylation - indoles - disulfides - sulfenylindoles - iodine

    References

  • 1 Funk CD. Nat. Rev. Drug Discovery  2005,  4:  664 
    CrossrefPubMedSearch in Google Scholar
  • 2a Unangst PC. Connor DT. Stabler SR. Weikert RJ. Carethers ME. Kennedy JA. Thueson DO. Chestnut JC. Adolphson RL. Conroy MC. J. Med. Chem.  1989,  32:  1360 
    Search in Google Scholar
  • 2b Armer RE, and Wynne GM. inventors; PCT Int. Appl. WO  2008012511. 
  • 3 La Regina G. Edler MC. Brancale A. Kandil S. Coluccia A. Piscitelli F. Hamel E. De Martino G. Matesanz R. Díaz JF. Scovassi AI. Prosperi E. Lavecchia A. Novellino E. Artico M. Silvestri R. J. Med. Chem.  2007,  50:  2865 
    Search in Google Scholar
  • 4a Williams TM, Ciccarone TM, Saari WS, Wai JS, Greenlee WJ, Balani SK, Goldman ME, Hoffman JM, Lumma WC, Huff JR, Rooney CS, Sanderson PE, and Theoharides AD. inventors; PCT Int. Appl. WO  9419321. 
  • 4b Silvestri R. Artico M. Bruno B. Massa S. Novellino E. Greco G. Marongiu ME. Pani A. De Montis A. La Colla P. Antiviral Chem. Chemother.  1998,  9:  139 
    Search in Google Scholar
  • 4c Ragno R. Coluccia A. La Regina G. De Martino G. Piscitelli F. Lavecchia A. Novellino E. Bergamini A. Ciaprini C. Sinistro A. Maga G. Crespan E. Artico M. Silvestri R. J. Med. Chem.  2006,  49:  3172 
    Search in Google Scholar
  • 4d De Martino G. La Regina G. Coluccia A. Edler MC. Barbera MC. Brancale A. Wilcox E. Hamel E. Artico M. Silvestri R. J. Med. Chem.  2004,  47:  6120 
    Search in Google Scholar
  • 5a Berger JP. Doebber TW. Leibowitz M. Moller DE. Mosley RT. Tolman RL. Ventre J. Zhang BB. Zhou G. PCT Int. Appl. WO 0130343,  2001, 
  • 5b Ramakrishna VSN, Shirsath VS, Kambhampati RS, Vishwakarma S, Kandikere NV, Kota S, and Jasti V. inventors; PCT Int. Appl. WO  2007020653. 
  • 6a Raban M. Chern L. J. Org. Chem.  1980,  45:  1688 
    Search in Google Scholar
  • 6b Ranken PF. McKinnie BG. J. Org. Chem.  1989,  54:  2985 
    Search in Google Scholar
  • 6c Browder CC. Mitchell MO. Smith RL. el-Sulayman G. Tetrahedron Lett.  1993,  34:  6245 
    Search in Google Scholar
  • 6d Hamel P. Préville P. J. Org. Chem.  1996,  61:  1573 
    Search in Google Scholar
  • 6e Hamel P. Tetrahedron Lett.  1997,  38:  8473 
    Search in Google Scholar
  • 6f Hamel P. J. Org. Chem.  2002,  67:  2854 
    Search in Google Scholar
  • 7 Matsugi M. Murata K. Gotanda K. Nambu H. Anilkumar G. Matsumoto K. Kita Y. J. Org. Chem.  2001,  66:  2434 
    CrossrefPubMedSearch in Google Scholar
  • 8 Tudge M. Tamiya M. Savarin C. Humphrey GR. Org. Lett.  2006,  8:  565 
    CrossrefPubMedSearch in Google Scholar
  • 9a Anzai K. J. Heterocycl. Chem.  1979,  16:  567 
    Search in Google Scholar
  • 9b Plate R. Nivard RJF. Ottenheijm HCJ. Tetrahedron  1986,  42:  4503 
    Search in Google Scholar
  • 9c Atkinson JG. Hamel P. Girard Y. Synthesis  1988,  480 
  • 9d Bunker AM. Edmunds JJ. Berryman KA. Walker DM. Flynn MA. Welch KM. Dohery AM. Bioorg. Med. Chem. Lett.  1996,  6:  1367 
    Search in Google Scholar
  • 10c Schlosser KM. Krasutsky AP. Hamilton HW. Reed JE. Sexton K. Org. Lett.  2004,  6:  819 
    Search in Google Scholar
  • 10a Campbell JA. Broka CA. Gong L. Walker KAM. Wang J.-H. Tetrahedron Lett.  2004,  45:  4073 
    Search in Google Scholar
  • 10b Yadav JS. Reddy BVS. Reddy YJ. Tetrahedron Lett.  2007,  48:  7034 
    Search in Google Scholar
  • 10d Maeda Y. Koyabu M. Nishimura T. Uemura S. J. Org. Chem.  2004,  69:  7688 
    Search in Google Scholar
  • For the synthesis of sulfenylindoles via the cyclization reactions of 2-(1-alkynyl)benzamides with sulfenyl chlorides or disulfides, see:
  • 11a Chen Y. Cho C.-H. Larock RC. Org. Lett.  2009,  11:  173 
    Search in Google Scholar
  • 11b Guo Y.-J. Tang R.-Y. Li J.-H. Zhong P. Zhang X.-G. Adv. Synth. Catal.  2009,  in press
  • For other papers on transition-metal-catalyzed thiation of phenols and 2-phenylpyridine, see refs. 6b, 10d and:
  • 12a Ranken PF. McKinnie BG. Synthesis  1984,  117 
  • 12b Chen X. Hao X.-S. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc.  2006,  128:  6790 
    Search in Google Scholar
  • 12c Yadav JS. Reddy BVS. Reddy YJ. Praneeth K. Synthesis  2009,  1520 
  • For reviews on the use of Fe catalysts, see:
  • 13a Bolm C. Legros J. Le Paih J. Zani L. Chem. Rev.  2004,  104:  6217 
    Search in Google Scholar
  • 13b Fürstner A. Martin R. Chem. Lett.  2005,  34:  624 
    Search in Google Scholar
  • 13c Iron Catalysis in Organic Chemistry: Reactions and Applications   Plietker B. Wiley-VCH; Weinheim: 2008. 
  • 13d Correa A. Mancheño OG. Bolm C. Chem. Soc. Rev.  2008,  37:  1108 
    Search in Google Scholar
  • 13e Sherry BD. Fürstner A. Acc. Chem. Res.  2008,  41:  1500 
    Search in Google Scholar
  • 14 Wu GL. Wu J. Wu JL. Wu LM. Synth. Commun.  2008,  38:  1036 
    CrossrefSearch in Google Scholar
  • 15 Zhao XD. Yu ZK. Xu TY. Wu P. Yu HF. Org. Lett.  2007,  9:  5263 
    CrossrefSearch in Google Scholar