jo0c01251_si_001.pdf (22.09 MB)
Three-Component Iminolactonization Reaction via Bifunctionalization of Olefins Using Molecular Iodine and Visible Light
journal contribution
posted on 2020-08-07, 12:04 authored by Saki Maejima, Eiji Yamaguchi, Akichika ItohA 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.