TFFH as an Excellent Reagent for Acylation of Alcohols, Thiols and Dithiocarbamates
Michael Pittelkow, Fadhil S. Kamounah, Ulrik Boas, Brian Pedersen, Jørn B. Christensen*
*Department of Chemistry, University of Copenhagen, Universitetsparken 5,
2100 Copenhagen, Denmark, Email: jbc
kiku.dk
M. Pittelkow, F. S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen, Synthesis, 2004, 2485-2492.
DOI: 10.1055/s-2004-831250
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Abstract
A convenient procedure allows the synthesis of esters and thioesters from the corresponding carboxylic acid using TFFH as the coupling reagent. The preparation of N-acyl-dithiocarbamates from carboxylic acids and 1,3-thiazolidine-2-thione is also described.
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Details
The document discusses the use of Tetramethylfluoroformamidinium hexafluorophosphate (TFFH) as an effective reagent for acylation reactions, specifically for synthesizing esters, thioesters, and N-acyl-dithiocarbamates from carboxylic acids. TFFH, introduced by Carpino and co-workers, is highlighted for its ease of handling, long shelf-life, and high reactivity, making it a superior alternative to traditional reagents like DCC, which has limitations such as low reactivity and high toxicity. The document details various procedures and examples demonstrating the versatility of TFFH in different solvents and conditions, achieving high yields with minimal side reactions. The synthesis of esters and thioesters via in situ acid fluoride formation and the chemoselective acylation of dithiocarbamates are emphasized. The document also provides specific examples and yields of compounds synthesized using TFFH, showcasing its broad compatibility with various functional groups. Overall, TFFH is presented as a valuable reagent in organic chemistry for efficient and mild acylation processes.
Key Words
esterification, coupling reagents, acylations (alcohols, thiols), esters, thioesters, thioacids, dithiocarbamates
ID: J66-Y2004-2350
