As a twofold Michael system, the diarylideneacetone core is of particular interest
in organic synthesis and for therapeutic applications. To overcome the drawbacks of
the classical Claisen–Schmidt protocol, a new methodology for the synthesis of dissymmetric
(hetero)diarylideneacetones has been developed. Conditions were optimized with a Box–Behnken
design of experiment. The milder reaction conditions allow the efficient preparation
of fluorinated, or heteroaromatic, dissymmetric diarylideneacetones which cannot be
obtained through the classical Claisen–Schmidt protocol.
Key words
heterocycles - catalysis - cross-coupling - isomerization - palladium - solvent effects
- substituent effects
