A Paternò–Büchi Reaction of Aromatics with Quinones under Visible Light Irradiation

oleh: Wen-Wen Li, Jia-Lin Zhao, Ze-Yu Wang, Pei-Ting Li, Zi-Fa Shi, Xiao-Ping Cao, Qiang Liu

Format: Article
Diterbitkan: MDPI AG 2024-03-01

Deskripsi

Reported herein is a Paternò–Büchi reaction of aromatic double bonds with quinones under visible light irradiation. The reactions of aromatics with quinones exposed to blue LED irradiation yielded oxetanes at −78 °C, which was attributed to both the activation of double bonds in aromatics and the stabilization of oxetanes by thiadiazole, oxadiazole, or selenadiazole groups. The addition of Cu(OTf)<sub>2</sub> to the reaction system at room temperature resulted in the formation of diaryl ethers via the copper-catalyzed ring opening of oxetanes in situ. Notably, the substrate scope was extended to general aromatics.