Polystyrene-bound thioxanthone – a heterogeneous photocatalyst for alcohol oxidation via singlet oxygen production

Abstract

We have synthesized a photocatalyst in which thioxanthone is covalently attached on a polystyrene (TX@PS) polymer and investigated its activity in the photocatalytic oxidation of alcohols to aldehydes. Upon LED irradiation (405 nm), benzyl alcohol is converted to benzaldehyde at a yield of 73% and hydroxymethylfurfural forms formic acid at 99%. Employing the photocatalyst for consecutive runs (up to three) results in product yields of 51% for the oxidation of benzaldehyde and 98% for hydroxymethylfurfural. EPR provides evidence that the oxidation proceeds via a singlet oxygen route. This proof-of-concept study shows that TX@PS can straightforwardly be prepared. Using this catalyst provides yields reflecting comparable systems and allows a convenient isolation of the products.