Anupama Datta, K. Ebert, H. Plenio
Oct 3, 2003
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Organometallics
Abstract
The anionic polymerization of 4-methylstyrene results in a linear poly(4-methylstyrene), whose substoichiometric bromination with Br2 converts a portion of 5−18% of the −CH3 units into −CH2Br groups, which were then reacted with (1-Ad)2PH to synthesize a polymer loaded with sterically demanding and electron-rich −CH2P(1-Ad)2 groups as the respective air-stable phosphonium salt. Palladium complexes with the phosphinated polymer are efficient catalysts for carbon−carbon coupling reactions of the Sonogashira, Suzuki, and Heck type with aryl chlorides and bromides. The molecular weight of the respective phosphines in the range of 5−35 kDa does not have a significant effect on the catalytic performance. Such polymer-enlarged catalysts are suitable for separation over a solvent-resistant nanofiltration membrane composed of a dense poly(dimethylsiloxane) (PDMS) layer cast on a porous sublayer of poly(acrylonitrile) (PAN). The membrane displays virtually quantitative retention of the polymeric catalyst; furthermo...