American Chemical Society
Browse
jo0c01251_si_001.pdf (22.09 MB)

Three-Component Iminolactonization Reaction via Bifunctionalization of Olefins Using Molecular Iodine and Visible Light

Download (22.09 MB)
journal contribution
posted on 2020-08-07, 12:04 authored by Saki Maejima, Eiji Yamaguchi, Akichika Itoh
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.

History