Phosphino carboxylic acid ester functionalized carbosilane dendrimers: nanoscale ligands for the Pd-catalyzed hydrovinylation reaction in a membrane reactor

EB Eggeling; NJ Hovestad; JT Jastrzebski; D Vogt; van Koten G

doi:10.1021/jo000433k

Phosphino carboxylic acid ester functionalized carbosilane dendrimers: nanoscale ligands for the Pd-catalyzed hydrovinylation reaction in a membrane reactor

J Org Chem. 2000 Dec 29;65(26):8857-65. doi: 10.1021/jo000433k.

Authors

EB Eggeling¹, NJ Hovestad, JT Jastrzebski, D Vogt, van Koten G

Affiliation

¹ Schuit Institute of Catalysis, Laboratory of Inorganic Chemistry and Catalysis, Eindhoven University of Technology, 5600 MB Eindhoven, The Netherlands, and Debye Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, 35.

PMID: 11149826
DOI: 10.1021/jo000433k

Abstract

Phosphino carboxylic acid ester terminated G(0) compounds Si(CH(2))(3)SiMe(2)(C(6)H(4)CH(2)OC(O)(CH(2))(n)()CH(2)PPh(2)(4) (9a and 9b; n = 1, 2) and the carbosilane dendrimers Si(CH(2))(3)Si((CH(2))(3)SiMe(2)(C(6)H(4)CH(2)OC(O)(CH(2))(n)()CH(2) PPh(2))(3)(4) (10a and 10b; n = 1, 2) have been prepared as hemilabile nanoscale ligands for the palladium-catalyzed codimerization of olefins. The hydrovinylation of styrene was carried out in a continuously operated nanofiltration membrane reactor. Under continuous conditions, the selectivity of the reaction is increased considerably. Monomeric model complexes and the dendritic catalysts were compared for their activity and selectivity in batch reactions. The Pd catalyst complexes were prepared in situ from the dendritic ligands and an (allyl)palladium(II) precursor.