Download PDF
Synlett 2012(3): 480-481  
DOI: 10.1055/s-0031-1290134
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Diphenylvinylsulfonium Triflate

Sven P. Fritz*
School of Chemistry, University of Bristol, Cantock’s Close, ­Bristol, BS8 1TS, UK
e-Mail: sven.fritz@bristol.ac.uk;
Further Information

Publication History

Publication Date:
25 January 2012 (online)

   Permissions and Reprints All articles of this category

Introduction

Diphenylvinylsulfonium triflate (1) is a pale, yellow, stable and free-flowing oil. It can easily be prepared from its commercially available precursor diphenylbromoethylsulfonium triflate (2, Scheme  [¹] ). Alternatively, it is also possible to generate vinylsulfonium salt 1 in situ from bromide 2.

Nucleophiles readily undergo conjugate addition to vinylsulfonium salts to form sulfur ylide intermediates, which can undergo a range of further transformations.

Extensive use in epoxidation, aziridination and other annulation reactions has shown the wide applicability of vinylsulfonium salts as two-carbon bridges.

Scheme 1 Preparation of diphenylvinylsulfonium triflate (1).

    References

  • 1a Kim KH. Jimenez LS. Tetrahedron: Asymmetry  2001,  12:  999 
    Search in Google Scholar
  • 1b Wang YF. Zhang WH. Colandrea VJ. Jimenez LS. Tetrahedron  1999,  55:  10659 
    Search in Google Scholar
  • 1c Dong WT. Jimenez LS. J. Org. Chem.  1999,  64:  2520 
    Search in Google Scholar
  • 1d Wang Z. Jimenez LS. Tetrahedron Lett.  1996,  37:  6049 
    Search in Google Scholar
  • 1e Wang Z. Jimenez LS. J. Am. Chem. Soc.  1994,  116:  4977 
    Search in Google Scholar
  • 2a Unthank MG. Hussain N. Aggarwal VK. Angew. Chem. Int. Ed.  2006,  45:  7066 
    Search in Google Scholar
  • 2b Kokotos CG. McGarrigle EM. Aggarwal VK. Synlett  2008,  2191 
  • 2c Unthank MG. Tavassoli B. Aggarwal VK. Org. Lett.  2008,  10:  1501 
    Search in Google Scholar
  • 2d McGarrigle EM. Yar M. Unthank MG. Aggarwal VK. Chem. Asian. J.  2011,  6:  372 
    Search in Google Scholar
  • 3 Catalan-Munoz S. Muller CA. Ley SV. Eur. J. Org. Chem.  2010,  183 
  • 4a Yar M. McGarrigle EM. Aggarwal VK. Angew. Chem. Int. Ed.  2008,  47:  3784 
    Search in Google Scholar
  • 4b Bornholdt J. Felding J. Kristensen JL. J. Org. Chem.  2010,  75:  7454 
    Search in Google Scholar
  • 4c Burkhard JA. Wagner B. Fischer H. Schuler F. Muller K. Carreira EM. Angew. Chem. Int. Ed.  2010,  49:  3524 
    Search in Google Scholar
  • 5 Yar M. McGarrigle EM. Aggarwal VK. Org. Lett.  2009,  11:  257 
    Search in Google Scholar
  • 6 Fritz SP. Mumtaz A. Yar M. McGarrigle EM. Aggarwal VK. Eur. J. Org. Chem.  2011,  3156 
  • 7 Chen JR. An J. Chang NJ. Song LD. Jin YQ. Ma Y. Xiao WJ. Chem. Commun.  2011,  47:  1869 
    Search in Google Scholar
  • 8 Xie CS. Han DY. Liu JH. Xie T. Synlett  2009,  3155 
  • 9 Xie CS. Han DY. Hu Y. Liu JH. Xie TA. Tetrahedron Lett.  2010,  51:  5238 
    Search in Google Scholar
  • 10 McGarrigle EM. Fritz SP. Favereau L. Yar M. Aggarwal VK. Org. Lett.  2011,  13:  3060 
    Search in Google Scholar
  • 11 Yar M. Fritz SP. Gates PJ. McGarrigle EM. Aggarwal VK. Eur. J. Org. Chem.  2012,  160