Fluorous Schiff base

Using a fluorous palladacycle catalyst 10 originating from the corresponding fluorous Schiff base and palladium acetate, a fluorous Mizoroki-Heck reaction was achieved with an excellent turnover number (Scheme 12). A homogeneous catalytic reaction system was obtained when DMF was used as the solvent. After the reaction, perfluorooctyl bromide was added to facilitate the separation of DMF (containing the products and amine salts) from the catalyst phase. The resulting lower fluorous layer was condensed under vacuum and the catalyst residue was used in a second run. In this reaction, the palladacycle catalyst appears to act as a source of palladium nanoparticles, which are thought to be the dominant active catalyst. 

The nickel complex 11, with a fluorous Schiff base as ligand, was prepared from salicylaldehyde and 4-perfluorodecylaniline (Scheme 15). This fluorous Ni complex was used as a catalyst for the conjugate addition of -diketones to diethyl azodicarboxylate (DEAD). The mixture was stirred at 60 C in a mixture of... 

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