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
Abstract:
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.