Download PDF
Synthesis 2003(10): 1541-1544
DOI: 10.1055/s-2003-40521
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Convenient One-Pot Synthesis of 4-(Dialkylaminobenzyl)triphenylphosphonium Salts - Application to the Synthesis of a Fluorescent Probe for Multiphotonic Imaging of Biological Membranes

Laurent Porrès, Bharath Kumar Goud Bhatthula, Mireille Blanchard-Desce*
Synthèse et ElectroSynthèse Organiques (CNRS, UMR 6510) , Université de Rennes 1, Campus de Beaulieu, Bât. 10A, 35042 Rennes Cedex, France
Fax: +33(2)23236277; e-Mail: Mireille.Blanchard-Desce@univ-rennes1.fr;
Further Information

Publication History

Received 18 April 2003
Publication Date:
08 July 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient one-pot preparation of (dialkylaminobenzyl)triphenylphosphonium salts directly from dialkylbenzenamine is described. The one-pot procedure proceeds quickly in high yields and allows the synthesis of useful reagents for Wittig reaction. Their potential is illustrated by the synthesis of a bolaamphiphilic fluorophore of interest for biological membrane imaging.

Key words

phosphorus - amines - Wittig reactions - alkenation - fluorescence­ - conjugation

    References

  • 1a Maryanoff BE. Reitz AB. Chem. Rev.  1989,  89:  863 
    Google Scholar
  • 1b Nicolaou KC. Harter MW. Gunzner JL. Nadin A. Liebigs Ann. Recueil.  1997,  1283 
    Google Scholar
  • 2a Londergan T, Todorova G, Zhu J, and Huang D. inventors; WO  0214305. 
    Crossref
  • 2b Maertens C. Zhang J.-X. Dubois P. Jérôme R. J. Chem. Soc., Perkin Trans. 2  1996,  713 
    CrossrefGoogle Scholar
  • 2c Marder S, and Perry J. inventors; US  6267913. 
    Crossref
  • 2d Segura JL. Gomez R. Martin N. Guldi DM. Org. Lett.  2001,  3:  2645 
    CrossrefGoogle Scholar
  • 2e Rumi M. Ehrlich JE. Heikal AA. Perry JW. Barlow S. Hu Z. McCord-Maughon D. Parker TC. Röckel H. Thayumanavan S. Marder SR. Beljonne D. Brédas J.-L. J. Am. Chem. Soc.   2000,  122:  9500 
    CrossrefGoogle Scholar
  • 3a Puccetti G. Blanchard-Desce M. Ledoux I. Lehn JM. Zyss J. J. Phys. Chem.  1993,  97:  9385 
    CrossrefGoogle Scholar
  • 3b Alain V. Redoglia S. Blanchard-Desce M. Lebus S. Lukaszuk K. Wortmann R. Gubler U. Bosshard C. Gunter P. Chem. Phys.  1999,  245:  51 
    CrossrefGoogle Scholar
  • 3c Brunel J. Ledoux I. Zyss J. Blanchard-Desce M. Chem. Commun.  2001,  923 
    CrossrefGoogle Scholar
  • 4 Banner BL, and Weber G.-F. inventors; US  5451600. 
  • An alternative proceeds directly from the alcohol by using the Ph3P˙HBr salt, but this procedure requires high thermal activation and a costly reagent:
  • 5a Zhang J.-X. Dubois P. Jérôme R. Synth. Commun.  1996,  26:  3091 
    Google Scholar
  • 5b Samyn C. Heylen M. Claes G. Boutton C. Van Beylen M. Persoons A. Eur. Polym. J.  1998,  34:  1069 
    Google Scholar
  • 6 Bredereck H. Simchen G. Griebenow W. Chem. Ber.  1973,  106:  3732 
    Google Scholar
  • 7 Dalton LR, Jen AK.-Y, Londergan T, Carlson WB, Phelan G, Huang D, Casmier D, Ewy T, and Buker N. inventors; WO  0208215. 
  • 8a Ventelon L. Charier S. Moreaux L. Mertz J. Blanchard-Desce M. Angew. Chem. Int. Ed.  2001,  40:  2098 
    Google Scholar
  • 8b Blanchard-Desce M. C. R. Physique  2002,  3:  439 
    Google Scholar
  • 8c Porrès L. Mongin O. Bhatthula BKG. Blanchard-Desce M. Ventelon L. Moreaux L. Pons T. Mertz J. Proc. SPIE-Int. Soc. Opt. Eng.  2002,  4812:  24 
    Google Scholar