Stilbene synthesis through decarboxylative cross-coupling of substituted cinnamic acids with aryl halides

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The Pd-catalyzed decarboxylative cross-coupling reaction between cinnamic acid and aryl iodide derivatives was studied using both homogeneous and heterogeneous Pd-catalysts. It was demonstrated that simple Pd(OAc)2 can catalyze this reaction with useful to high yields when engaging ferulic acid whatever the nature of the aryl iodide. However, limitations were found when varying the nature of the cinnamic acid derivatives mainly due to low decarboxylation process. This could be overcome in some cases by adding Cu(OH)2/1,10-phenantroline as co-catalyst. In the presence of heterogeneous catalysts, the studies showed that both Pd/C and home-made Pd/SiO2 catalysts afforded high product yields; however, while less active it was demonstrated that the Pd/SiO2 catalyst could be reused over at least 4 cycles due to higher stability.