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reaction: see text The fluorous Schiff base p-Rf8(CH2)3C6H4C(=N(CH2)3Rf8)(CH2)2Rf8 (Rf8 = n-C8F17) is prepared in six steps from p-iodobenzaldehyde and then cyclopalladated (Pd(OAc)2) to give highly effective catalyst precursors for Heck reactions, conducted under homogeneous conditions (DMF, 80-140 degrees C, turnover numbers >10(6)) in the absence of fluorous solvents. Rate, recycling, and other data suggest that the palladacycles serve as sources of palladium nanoparticles, which are the dominant active catalysts.
Rocaboy et al. (2002) studied this question.