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Updated: Jun 27, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Direct synthesis of acyl fluorides from carboxylic acids using benzothiazolium reagents
Lilian M Maas1,2, Alex Haswell2, Rory Hughes2
1Institute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34-36, 14195 Berlin, Germany.
Abstract:
2-(Trifluoromethylthio)benzothiazolium triflate (BT-SCF3) was used as deoxyfluorinating reagent for the synthesis of versatile acyl fluorides directly from the corresponding carboxylic acids. These acyl fluorides were reacted with amines in a one-pot protocol to form different amides, including dipeptides, under mild and operationally simple conditions in high yields. Mechanistic studies suggest that BT-SCF3 can generate acyl fluorides from carboxylic acids via two distinct pathways, which allows the deoxyfluorinating reagent to be employed in sub-stoichiometric amounts.
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