Hui Zhang, Ke-Chun Wang, Wei-Jun Cao, Ying-Jie Wang, Peng-Fei Xu*
https://doi.org/10.1002/ejoc.70504
Abstract
Herein, we report a synthetic strategy that relies on a self-developed organic photocatalyst for the efficient construction of imidazolines and oxazolidines. Using readily available 4-methyl-N-(2-phenylallyl)benzenesulfonamide alkenes and redox-active esters (RAEs) or aryl diazonium tetrafluoroborates as substrates, the reaction proceeds in acetonitrile/acetone via photoredox-initiated radical addition followed by ionic cyclization, which involves the formation of a key nitrilium/imidate-type ionic intermediate. This transformation features mild reaction conditions and facile operation, not only expanding the application scope of the developed photocatalyst, but also providing a practical technical platform for the photocatalytic synthesis of structurally diverse bioactive molecules containing imidazoline and oxazolidine motifs.