APPLICATION OF SONOGASHIRA AND BAYLIS-HILLMAN REACTIONS WITH TRIFLUOROMETHYLATED ACROLEINS BY USING PALLADIYM(0) AND N-METHYLIMIDAZOLE AS CATALYSIS
Emna Zouaoui and Mohamed Moncef El Gaïed
Département de Génie de Procédés et Pétrochimie, Faculté de Technologie université de 20Aout 1955 Skikda Algérie
Organofluorine compounds have found increasing use in the areas of agrochemicals, pharmaceuticals, polymers and new materials.1-3 The fluorine atom brings specific chemical and physical properties to molecules in the pharmaceutical field. Molecules containing CF2 or CF3 can offer a significant change in biological activity, compared to their non fluorinated analogs. For example, the enzyme inhibitory activity of trifluoromethylketones has been widely proved.4-5 The interest in molecules containing the CF3 group entailed the development of new and efficient synthetic methodologies.
Particularly, the formation of C-C bond and the transformation of functional groups are fundamentals process for organic synthesis. Recently, the catalysis by the transition metals and Baylis-Hillman reaction are strongly influenced this research area during these last years 6
In connection with on going interests in the synthesis and the reactivity of trifluoromethylated Vilsmeir adducts7-8, we are interested at the action of alkynes compounds towards 2-phenyl-3-iodo-4,4,4-trifluorobut-2-enal in the presence of palladium (0) is reported according to the reaction of Sonogashira. Moreover, 2-(hydroxytrifluoro-methylalkenyl)cyclohexenones have been prepared by the reaction of cyclohexenone and β -trifluromethylacroleins in the presence of N-methylimidazole catalysis.
Keywords: β-trifluoromethylenynes, palladium (0), cyclohexenone, N-methylimidazol catalysis and Baylis-Hillman adducts.