A structure–activity relationship study on the Wacker oxidation of stilbenes at ambient condition

•The study on Wacker oxidation of cyclic and internal stilbenes with PdCl2.•The study of the structural elements of the stilbenes on the Wacker oxidation.•The oxidation rate of stilbenes was strongly depended on their structures.•The ortho position of alkene and methoxy groups on stilbenes plays a key role.•Cyclic stilbene shows a higher efficiency due to host–guest complexation.

To evaluate which structural elements of the stilbenes are responsible for their activity on the Wacker oxidation, a series of stilbenes with various functional moieties and substitution patterns were considered. In this regard, it is found that the oxidation rate of stilbenes strongly depends on their structures to give the corresponding carbonyl compounds. Consequently, the ortho position of alkene and methoxy groups plays a key role in the complexation with PdCl2. The oxidation process is clean with high selectivity of product and low percentage of byproducts.

Graphical abstractIt is found that the Wacker oxidation rate of stilbenes strongly depends on their structures and, consequently, the ortho position of alkene and methoxy groups plays a key role in the complexation with PdCl2. The oxidation process is clean with high selectivity of product and low percentage of byproducts.Figure optionsDownload full-size imageDownload as PowerPoint slide