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Highly active thermomorphic fluorous palladacycle catalyst precursors for the Heck reaction; evidence for a palladium
Christian Rocaboy1, J A Gladysz
1Institut für Organische Chemie, Friedrich-Alexander Universität Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen, Germany.
Organic Letters
|June 7, 2002
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.