Work

Direct oxygen insertion into C-C bond of styrenes with air

Year: 2024

Type: article

Abstract: Skeletal editing of single-atom insertion to basic chemicals has been demonstrated as efficient strategy for the discovery of structurally novel compounds. Previous endeavors in skeletal editing have successfully facilitated the insertion of boron, nitrogen, and carbon atoms. Given the prevalence of oxygen atoms in biologically active molecules, the direct oxygenation of C-C bonds through single-oxygen-atom insertion like Baeyer-Villiger reaction is of particular significance. Herein, we present a novel approach for the skeletal modification of styrenes using O2 via oxygen insertion into Ar-C(sp2) σ-bond, resulting in the formation of corresponding aryl ether frameworks under mild reaction conditions. The broad functional-group tolerance and the excellent chemo- and regioselectivity were demonstrated in this protocol. A preliminary mechanistic study indicated the potential involvement of 1,2-aryl radical migration in this reaction.

Source: Nature Communications

DOI: 10.1038/s41467-024-53266-6