Shi Tongtong, Tian Miao, Sun Zongfei, Zou Ruixiao, Zhang Zexuan, Xie Na, Hao Erjun, Xu Xinming, Sun Kai
School of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, P. R. China.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, P. R. China.
Chem Commun (Camb). 2025 Mar 4;61(20):4066-4069. doi: 10.1039/d4cc06686c.
Indole-fused medium-sized diazepinones are privileged structural motifs found in many high-value pharmaceuticals. To construct these challenging molecular skeletons, previous methods are mainly achieved by [5+2] annulation strategies with the aid of transition metal (Pd, Rh, Ru) catalyzed oxidative C-H coupling. Herein, we report a novel visible-light-induced sulfonylation-cyclization-selenylation reaction for the rapid construction of highly functionalized indole-fused medium-sized diazepinones with biomass feedstock 2-Me-THF as the medium. Based on the mechanism studied, an electrophilic radical sulfonylation-cyclization and subsequent aerobic electrophilic C-3 selenylation route is proposed.
