PVA-PEG Resin-Supported TEMPO

Significance

Poly(vinyl alcohol)-poly(ethylene glycol) graft polymer-resin was developed as a novel polymeric support for solid-phase organic synthesis. Linear poly(vinyl alcohol) 1 was cross-linked with epichlorohydrin under alkaline conditions to afford PVA resin beads 2 (an optical micrograph and an SEM image were provided). Synthetic utilities of the PVA resin were examined for the solid-phase peptide synthesis via the standard Fmoc method as well as the click [3+2] cycloaddition by way of polymeric azide 4. An amphiphilic resin-supported TEMPO reagent 6 was prepared via the click introduction of the TEMPO unit onto the PVA azide resin 4. The PVA-TEMPO 6 efficiently promoted oxidation of various alcohols (6 examples) with aqueous sodium hypochlorite under biphasic conditions (CH₂Cl₂-H₂O).