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 CF3 radical 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.