Heck Cross-Coupling for Synthesizing Metal-Complexing Monomers

Abstract

New polymerizable ligands for complexing metal ions have been synthesized. The polymerizable ligands were made by Heck cross-coupling of aromatic bromides with high pressure ethylene gas under mild conditions at room temperature. The vinyl substituted ligands were prepared in good yields and characterized by GC-MS, FT-NMR, FT-IR and microanalysis.

Key words

Heck reaction - alkenes - cross-coupling - β-diketones - monomers

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6

4-Vinyl methylbenzoate was prepared in three steps starting with the bromination of 4-methyl methylbenzoate with NBS. The product, 4-bromomethyl methylbenzoate was converted to the phosphonium salt by reaction with triphenylphos-phine. Finally, 4-vinyl methylbenzoate was formed via Witting coupling of the corresponding phosphonium salt with formaldehyde.