PDF herunterladen
Synlett 2010(10): 1557-1561  
DOI: 10.1055/s-0029-1219947
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Tantalum Carbide or Niobium Carbide Catalyzed Oxidation of Sulfides with Hydrogen Peroxide: Highly Efficient and Chemoselective Syntheses of Sulfoxides and Sulfones

Masayuki Kirihara*, Atsushi Itou, Takuya Noguchi, Junya Yamamoto
Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan
Fax: +81(538)450110; e-Mail: kirihara@ms.sist.ac.jp;
Weitere Informationen

Publikationsverlauf

Received 22 February 2010
Publikationsdatum:
25. Mai 2010 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

The oxidation of sulfides with 30% hydrogen peroxide catalyzed by tantalum carbide provided the corresponding sulfoxides in high yields. The reaction of sulfides with 30% hydrogen peroxide catalyzed by niobium carbide efficiently afforded the corresponding sulfones. These catalysts can easily be recovered from the reaction mixture and may be repeatedly used as catalysts for the oxidation without losing their activity.

Key words

tantalum carbide - niobium carbide - hydrogen peroxide - sulfide - recyclable catalyst

    References and Notes

  • 1 CRC Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Data   90th ed.:  David LR. CRC Press; Boca Raton / FL: 2009. 
    Google Scholar
  • 2a Kirihara M. Yamamoto J. Noguchi T. Hirai H. Tetrahedron Lett.  2009,  50:  1180 
    Google Scholar
  • 2b Kirihara M. Yamamoto J. Noguchi T. Itou A. Naito S. Hirai Y. Tetrahedron  2009,  65:  10477 
    Google Scholar
  • Reviews:
  • 3a Carreno MC. Chem. Rev.  1995,  95:  1717 
    Google Scholar
  • 3b Frenanez I. Khiar N. Chem. Rev.  2003,  103:  3651 
    Google Scholar
  • Oxidation of sulfides with hydrogen peroxide catalyzed by transition-metal compounds:
  • 4a Kaczorowska K. Kolarska Z. Mitka K. Kowalski P. Tetrahedron  2005,  61:  8315 
    Google Scholar
  • 4b Mba M. Prins LJ. Licini G. Org. Lett.  2007,  9:  21 
    Google Scholar
  • 4c Jeyakumar K. Chand K. Tetrahedron Lett.  2006,  47:  4573 
    Google Scholar
  • 4d Egami H. Katsuki T. J. Am. Chem. Soc.  2007,  129:  8940 
    Google Scholar
  • 4e Blakemore PR. Burge MS. J. Am. Chem. Soc.  2007,  129:  3068 
    Google Scholar
  • 4f Mohammadpoor-Baltok I. Hill M. Caggiano L. Jackson RFW. Synlett  2006,  3540 
    Google Scholar
  • 4g Sato K. Hyodo M. Aoki M. Zheng X.-Q. Noyori R. Tetrahedron  2001,  57:  2469 
    Google Scholar
  • 4h Shi X.-Y. Wei J.-F. J. Mol. Catal. A  2008,  280:  142 
    Google Scholar
  • 4i Yamazaki S. Bull. Chem. Soc. Jpn.  1996,  69:  2955 
    Google Scholar
  • 4j Kelly P. Lawrence SE. Maguire AR. Synlett  2007,  1501 
    Google Scholar
  • 4k Hosseinpoor F. Golchoubian H. Tetrahedron Lett.  2006,  47:  5195 
    Google Scholar
  • 4l Alonso DA. Nájera C. Varea M. Tetrahedron Lett.  2002,  43:  3459 
    Google Scholar
  • 4m Yuan Y. Bian Y. Tetrahedron Lett.  2007,  48:  8518 
    Google Scholar