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

Michael Pittelkow; Fadhil S. Kamounah; Ulrik Boas; Brian Pedersen; Jørn B. Christensen

doi:10.1055/s-2004-831250

PAPER

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

Michael Pittelkow^a, Fadhil S. Kamounah^b, Ulrik Boas^a, Brian Pedersen^a, 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

Abstract

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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.

Key words

esterification - coupling reagents - acylations - esters - thioesters - thioacids - dithiocarbamates

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References

<A NAME="RT05204SS-1A">1a</A> Albericio F. Chinchilla R. Dodsworth DJ. Najera C. Org. Prep. Proced. Int. 2001, 33: 203

<A NAME="RT05204SS-1B">1b</A> Han S.-Y. Kim Y.-A. Tetrahedron 2004, 60: 2447

<A NAME="RT05204SS-1C">1c</A> March J. Advanced Organic Chemistry 4th ed.: Wiley Interscience; New York: 1992. p.904

<A NAME="RT05204SS-2">2</A> Katritzky AR. Meth-Cohn O. Rees CW. Comprehensive Organic Functional Group Transformations Vol. 5: Elsevier; Oxford: 1995. p.121

<A NAME="RT05204SS-3">3</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999.

<A NAME="RT05204SS-4A">4a</A> Fieser LF. Fieser M. Reagents for Organic Synthesis Vol. 1: John Wiley & Sons; New York: 1967. p.231

<A NAME="RT05204SS-4B">4b</A> Paquette LA. Encyclopedia of Reagents for Organic Synthesis Vol. 3: John Wiley & Sons; West Sussex: 1995. p.1751

<A NAME="RT05204SS-5">5</A> Sheehan JC. Hess GP. J. Am. Chem. Soc. 1955, 77: 1067

<A NAME="RT05204SS-6A">6a</A> Sheehan JC. Henery-Logan KR. J. Am. Chem. Soc. 1957, 79: 1262

<A NAME="RT05204SS-6B">6b</A> Nicolaou KC. Sorensen EJ. In Classics in Total Synthesis Vol. 1: Corey EJ. VCH Publishers Inc.; New York: 1996.

<A NAME="RT05204SS-7">7</A> Holmberg K. Hansen B. Acta Chim. Scand. Ser. B 1979, 33: 410

<A NAME="RT05204SS-8A">8a</A> Isoobe T. Ishikawa T. J. Org. Chem. 1999, 64: 6984

<A NAME="RT05204SS-8B">8b</A> Fujisawa T. Tajima K. Sato T. Bull. Chem. Soc. Jpn. 1983, 56: 3529

<A NAME="RT05204SS-8C">8c</A> Fujisawa T. Mori T. Fukumoto K. Sato T. Chem. Lett. 1982, 1891

<A NAME="RT05204SS-8D">8d</A> Isobe T. Ishikawa T. J. Org. Chem. 1999, 64: 6989

<A NAME="RT05204SS-9">9</A> Carpino LA. El-Faham A. J. Am. Chem. Soc. 1995, 117: 5401

<A NAME="RT05204SS-10">10</A> Carpino LA. Ionescu D. El-Faham A. J. Org. Chem. 1996, 61: 2460

<A NAME="RT05204SS-11">11</A> El-Faham A. Abdul-Ghani M. Org. Prep. Proced. Int. 2003, 35: 369

<A NAME="RT05204SS-12">12</A> Boas U. Pedersen B. Christensen JB. Synth. Commun. 1998, 28: 1223

<A NAME="RT05204SS-13">13</A> Boas U. Gertz H. Christensen JB. Heegaard PMH. Tetrahedron Lett. 2004, 45: 269

Other procedures available for the preparation of TFFH include:

Ref. 9.

Ref. 10.

Ref. 11.

Ref. 12.

<A NAME="RT05204SS-14E">14e</A> Vojkovsky T. Drake B. Org. Prep. Proced. Int. 1997, 29: 497

For a general introduction to atom economy see:

<A NAME="RT05204SS-15A">15a</A> Trost BM. Acc. Chem. Res. 2002, 35: 695

<A NAME="RT05204SS-15B">15b</A> Trost BM. Angew. Chem., Int. Ed. Engl. 1995, 34: 259

<A NAME="RT05204SS-16A">16a</A> Fujita E. Nagao Y. Seno K. Takao S. Miyasaka T. Kimura M. Watson WH. J. Chem. Soc., Perkin Trans. 1 1981, 914

<A NAME="RT05204SS-16B">16b</A> Nagao Y. Kawabata K. Seno K. Fujita E. J. Chem. Soc., Perkin Trans. 1 1980, 2470

<A NAME="RT05204SS-17">17</A> Delmas M. Le Bigot Y. Gorrichon J.-P. Gaset A. Synth. Commun. 1982, 12: 327

<A NAME="RT05204SS-18">18</A> Beckmann CO. Zanetti JE. J. Am. Chem. Soc. 1926, 48: 1067

<A NAME="RT05204SS-19">19</A> Yale HL. J. Am. Chem. Soc. 1947, 69: 1230

<A NAME="RT05204SS-20">20</A> Grillot GF. Levin PM. Green R. Bashford RI. J. Am. Chem. Soc. 1950, 72: 1863