Radical Selenylative Cyclization of Trifluoromethyl Propargyl Imines for the Synthesis of Trifluoromethyl- and Seleno-azaspiro[4,5]-tetraenones and Quinolines

A radical selenylative cyclization of trifluoromethyl propargyl imines with diselenides for the regiodivergent construction of diversely functionalized azaspiro[4,5]-tetraenones and quinolines has been developed, which enables dual incorporation of CF and Se groups into heterocycles in a one-pot reaction. When using Oxone as a green oxidant, the reaction proceeds through oxidative dearomative -annulation or intramolecular -annulation exhibiting good regioselectivity. The synthetic utility of this method is demonstrated by a scale-up reaction and further modification of the obtained products.