2025 Volume 73 Issue 8 Pages 738-744
We report the catalyst-free aminoalkylation of alkenes, enabled by the formation of an electron donor–acceptor (EDA) complex between alkenes and amine-tethered N-hydroxyphthalimide (NHPI) esters. This visible-light induced transformation proceeds without external photocatalysts or additives. Spectroscopic and computational analyses support EDA complex formation, which undergoes photoinduced single-electron transfer to generate a radical ion pair that initiates C–N bond formation via intramolecular cyclization. The reaction exhibits a broad substrate scope, including electron-rich and electron-deficient alkenes, as well as structurally diverse NHPI esters, enabling access to various nitrogen-containing heterocycles such as pyrrolidines, benzodioxoles, and furan-fused frameworks. This operationally simple and modular method is a valuable platform for constructing biologically relevant molecules under mild conditions.
