Highly active thermomorphic fluorous palladacycle catalyst precursors for the Heck reaction; evidence for a palladium nanoparticle pathway |
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Authors: | Rocaboy Christian Gladysz J A |
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Institution: | Institut für Organische Chemie, Friedrich-Alexander Universit?t Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany. |
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Abstract: | 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. |
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