A general approach to fluorinated (hetero)aromatic derivatives is elaborated. The key reaction is a deoxofluorination of substituted acetophenones with sulfur tetrafluoride (SF 4 ). In contrast to previous deoxofluorination methods, this transformation is fast, scalable (up to 70 g), and high-yielding. More than 100 novel or previously hardly accessible fluorinated heterocycles, interesting for medicinal chemistry and agrochemistry, were synthesized.
CF3-cyclopropanes with aliphatic, aromatic,
and even
heteroaromatic substituents were prepared on a multigram scale by
deoxyfluorination of cyclopropane carboxylic acids or their salts
with sulfur tetrafluoride. For labile α-pyridine acetic acids,
only the use of their potassium salts allowed to obtain the needed
products. Derivatization of CF3-cyclopropanes into building
blocks ready for direct use in medicinal chemistry was performed.
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