Radical N2-Retention Cyclizations of Aryl Diazoniums: Access to 7/8/9-Membered Heterocycles

Autor: Ke, Sen, Jia, Yagang, Tong, Ye, Luo, Wencheng, Wu, Shufeng, Jiang, Xiangwen, Li, Yi
Zdroj: Organic Letters; May 2024, Vol. 26 Issue: 17 p3622-3627, 6p
Abstrakt: We report herein a modular approach to synthesizing diverse functionalized 7/8/9-membered poly-N-containing heterocycles via oxidative radical N2-retention cyclizations of allylic aryl diazonium salts using CF3SO2Na as a CF3radical source. A range of trifluoromethylated benzotriazepines, benzotriazocines, and benzotriazonines were obtained in moderate to good yields. This transition-metal-free protocol demonstrates atom economy, safe conditions, broad functional group tolerance, and availability of readily accessible reagents.
Databáze: Supplemental Index