Beilstein J. Org. Chem.2024,20, 921–930, doi:10.3762/bjoc.20.82
Kingdom 10.3762/bjoc.20.82 Abstract 2-(Trifluoromethylthio)benzothiazolium triflate (BT-SCF3) was used as deoxyfluorinating reagent for the synthesis of versatile acylfluorides directly from the corresponding carboxylic acids. These acylfluorides 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 acylfluorides from carboxylic acids via two distinct pathways, which allows the deoxyfluorinating reagent to be employed in sub-stoichiometric amounts
.
Keywords: acylfluorides; amides; benzothiazolium salts; carboxylic acids; deoxygenative reactions; Introduction
Acylfluorides are attracting much attention as versatile reagents for different applications in organic synthesis. In addition to their use as sources of fluoride ions, they are most commonly
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Graphical Abstract
Figure 1:
Advantages of acyl fluorides compared to acyl chlorides, previous work on BT-SRF reagents [29-33] and a su...
Beilstein J. Org. Chem.2020,16, 3052–3058, doi:10.3762/bjoc.16.254
the formation of trifluoromethyl compounds from acylfluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acylfluorides and resulted in the corresponding trifluoromethyl products with high
yields (up to 99%). This strategy showed a great tolerance for various acylfluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding
trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.
Keywords: acylfluorides; deoxyfluorination; fluorine; solvent-free; trifluoromethyl group; Introduction
Due to an impressively wide effect of fluorine on the biological activity, the insertion of fluorine atoms or
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Graphical Abstract
Figure 1:
Ratios of CF3-containing drugs in marketed fluoro-pharmaceuticals and registered fluoro-agrochemica...