(560dw) Self-Assembled Polymer Nanoreactors for Cascade Reactions

Confining catalyzed reactions to the hydrophobic core of micellar nanoreactors can facilitate organic phase reactions in a bulk aqueous environment with improved reaction kinetics due to enhanced localized reagent concentrations. The focus of this work was evaluating use of self-assembled core-shell polymer nanoreactors for the oxidation of benzyl alcohol to benzaldehyde followed by the reductive amination of benzaldehyde with 4-nitrophenol. Using polystyrene as a model hydrophobic microenvironment, the effect of base, oxidant, and reducing agent selection on benzyl alcohol oxidation were investigated. Potassium carbonate was found to provide higher benzyl alcohol conversion and benzaldehyde selectivity than organic, hydrophobic bases. Use of hydrogen peroxide as an oxidant resulted in a 10-fold increase in benzyl alcohol conversion compared to air. The effect of reducing agent, base selection, and relative reagent concentrations on the reductive amination of benzaldehyde will be discussed.