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Carbosilane Dendrons as Solubilizers of Metal Complexes in Supercritical Carbon Dioxide

Palladium complexes of general formula [PdCl2(L)2], 3a-c, were synthesized by reaction of [PdCl2(COD)] (COD = 1,5-cyclooctadiene) with the appropriate functionalized phosphine L = [P(C6H5)n((C6H4CH2CH2Si(CH2CH2CH2SiEtMe2)3)3-n)] (n = 2, 2a; 1, 2b; 0, 2c, respectively), which integrated carbosilane dendritic wedges attached to the para-carbon atom of the phenyl group. As a result of the inclusion of the carbosilane dendrons, the solubility of the corresponding palladium complexes 3 in supercritical carbon dioxide (scCO2) was increased in comparison with the palladium complex containing a PPh3 ligand, which showed negligible solubility. The employment of these complexes as precatalysts in a selected Heck coupling reaction in scCO2 was investigated. Good activities were found for 3a-c in such a medium due to the acquired solubility, in contrast with the palladium complex containing PPh3, which showed no activity.

Carbosilane dendrons as solubilizers of metal complexes in supercritical carbon dioxide

F. Montilla, A. Galindo, T. Andrés, M. Córdoba, E. de Jesús, C. Bo

Organometallics 2006, 25, 4138-4143
DOI: Go to the journal

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