Allylic hydroxylation of enones useful for the functionalization of relevant drugs and natural products.

ABSTRACT: Enones are privileged structural motifs in bioactive natural products and pharmaceuticals, but the γ-hydroxylation of enones is challenging. Here we show a mild and efficient method for the direct C(sp³)-H hydroxylation of enones via visible-light-induced hydrogen-atom transfer (HAT), which facilitates γ-hydroxylation of primary, secondary, and tertiary C-H bonds of different enones without involving metal and peroxide. The mechanism study shows that Na₂-eosin Y serves as both the photocatalyst and the source of catalytic bromine radical species in the HAT-based catalytic cycle, and finally sacrifices itself completely by oxidative degradation to produce bromine radical and a major product phthalic anhydride in an environmentally friendly way. This scalable method was

SUBMITTER: Zheng CY 

PROVIDER: S-EPMC10133259 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature