Synthesis 2004(15): 2485-2492  
DOI: 10.1055/s-2004-831250
PAPER
© Georg Thieme Verlag Stuttgart · New York

TFFH as an Excellent Reagent for Acylation of Alcohols, Thiols and Dithiocarbamates

Michael Pittelkowa, Fadhil S. Kamounahb, Ulrik Boasa, Brian Pedersena, Jørn B. Christensen*a
a Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark
Fax: +4535322012; e-Mail: jbc@kiku.dk;
b Department of Lifescience and Chemistry, Roskilde University, Universitetsvej 1, Postal Box 260, 4000 Roskilde, Denmark
Further Information

Publication History

Received 17 May 2004
Publication Date:
29 September 2004 (online)

Abstract

A convenient and easy procedure to synthesize esters and thioesters from the corresponding carboxylic acid using TFFH as the coupling reagent is described. The preparation of N-acyl-dithiocarbamates from carboxylic acids and 1,3-thiazolidine-2-thione with TFFH as the coupling reagent is also described.

    References

  • 1a Albericio F. Chinchilla R. Dodsworth DJ. Najera C. Org. Prep. Proced. Int.  2001,  33:  203 
  • 1b Han S.-Y. Kim Y.-A. Tetrahedron  2004,  60:  2447 
  • 1c March J. Advanced Organic Chemistry   4th ed.:  Wiley Interscience; New York: 1992.  p.904 
  • 2 Katritzky AR. Meth-Cohn O. Rees CW. Comprehensive Organic Functional Group Transformations   Vol. 5:  Elsevier; Oxford: 1995.  p.121 
  • 3 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999. 
  • 4a Fieser LF. Fieser M. Reagents for Organic Synthesis   Vol. 1:  John Wiley & Sons; New York: 1967.  p.231 
  • 4b Paquette LA. Encyclopedia of Reagents for Organic Synthesis   Vol. 3:  John Wiley & Sons; West Sussex: 1995.  p.1751 
  • 5 Sheehan JC. Hess GP. J. Am. Chem. Soc.  1955,  77:  1067 
  • 6a Sheehan JC. Henery-Logan KR. J. Am. Chem. Soc.  1957,  79:  1262 
  • 6b Nicolaou KC. Sorensen EJ. In Classics in Total Synthesis   Vol. 1:  Corey EJ. VCH Publishers Inc.; New York: 1996. 
  • 7 Holmberg K. Hansen B. Acta Chim. Scand. Ser. B  1979,  33:  410 
  • 8a Isoobe T. Ishikawa T. J. Org. Chem.  1999,  64:  6984 
  • 8b Fujisawa T. Tajima K. Sato T. Bull. Chem. Soc. Jpn.  1983,  56:  3529 
  • 8c Fujisawa T. Mori T. Fukumoto K. Sato T. Chem. Lett.  1982,  1891 
  • 8d Isobe T. Ishikawa T. J. Org. Chem.  1999,  64:  6989 
  • 9 Carpino LA. El-Faham A. J. Am. Chem. Soc.  1995,  117:  5401 
  • 10 Carpino LA. Ionescu D. El-Faham A. J. Org. Chem.  1996,  61:  2460 
  • 11 El-Faham A. Abdul-Ghani M. Org. Prep. Proced. Int.  2003,  35:  369 
  • 12 Boas U. Pedersen B. Christensen JB. Synth. Commun.  1998,  28:  1223 
  • 13 Boas U. Gertz H. Christensen JB. Heegaard PMH. Tetrahedron Lett.  2004,  45:  269 
  • Other procedures available for the preparation of TFFH include:
  • 14a

    Ref. 9.

  • 14b

    Ref. 10.

  • 14c

    Ref. 11.

  • 14d

    Ref. 12.

  • 14e Vojkovsky T. Drake B. Org. Prep. Proced. Int.  1997,  29:  497 
  • For a general introduction to atom economy see:
  • 15a Trost BM. Acc. Chem. Res.  2002,  35:  695 
  • 15b Trost BM. Angew. Chem., Int. Ed. Engl.  1995,  34:  259 
  • 16a Fujita E. Nagao Y. Seno K. Takao S. Miyasaka T. Kimura M. Watson WH. J. Chem. Soc., Perkin Trans. 1  1981,  914 
  • 16b Nagao Y. Kawabata K. Seno K. Fujita E. J. Chem. Soc., Perkin Trans. 1  1980,  2470 
  • 17 Delmas M. Le Bigot Y. Gorrichon J.-P. Gaset A. Synth. Commun.  1982,  12:  327 
  • 18 Beckmann CO. Zanetti JE. J. Am. Chem. Soc.  1926,  48:  1067 
  • 19 Yale HL. J. Am. Chem. Soc.  1947,  69:  1230 
  • 20 Grillot GF. Levin PM. Green R. Bashford RI. J. Am. Chem. Soc.  1950,  72:  1863