Diverse trifluoromethyl-substituted
compounds were synthesized
by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids
with sulfur tetrafluoride. The obtained products were used as starting
materials in the preparation of novel fluorinated amino acids, anilines,
and aliphatic amines - valuable building blocks for medicinal chemistry
and agrochemistry.
A practical method for the synthesis of functionalized aliphatic trifluoromethyl-substituted derivatives from aliphatic acids is developed. The transformation proceeds with sulfur tetrafluoride in the presence of water as a key additive. Compared to previous methods, the reaction gives products with full retention of stereo-and absolute configuration of chiral centers.
Pyroglutamic acid smoothly reacts with sulfur tetrafluoride at room temperature to afford enantiomerically pure (5S)-5-(trifluoromethyl)pyrrolidin-2-one (92 % yield, Ͼ99 % ee).
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