Three-Component Iminolactonization Reaction via Bifunctionalization of Olefins Using Molecular Iodine and Visible Light
Saki Maejima, Eiji Yamaguchi, Akichika Itoh
Abstract
A novel three-component γ-iminolactonization reaction was developed, which relied on the C-C/C-O bond-forming bifunctionalization of olefins using molecular iodine and visible light. This strategy did not require any (heavy) metal reagents for double-bond activation because molecular iodine acted as a rare-metal-alternative reagent through visible light irradiation. In addition, the preactivation of amines and other substrates is not required. The mechanistic investigation revealed that the generated iodine radicals under visible light irradiation reacted with alkenes to form a highly reactive intermediate; then, the three-component reaction of diiodide, malonate, and amine furnished iminolactone. Of note, the developed reaction is simple and realized the diversity-oriented synthesis innovative methodology of γ-iminolactone derivatives in drug discovery chemistry.