Remote difunctionalization of alkenes through a photocatalytically triggered radical clock and α-carbonyl carbocation generation.

ABSTRACT: The 1,5-difunctionalization of alkenes can precisely introduce functional groups at specific positions and create chiral centers, which is crucial for the development of complex drug molecules and functional materials. Here we show a photocatalytic, remote 1,5-difunctionalization of alkenes to achieve the synthesis of α,ε-difunctionalized γ,δ-unsaturated amides or esters. This three-component reaction of the amides or esters bearing a free radical clock moiety at α-carbon with Umemoto reagents (UR) and O/F/Cl-nucleophiles is initiated through an addition of CF₃ radical generated in situ by the photocatalytic fragmentation of UR to the double-bond, triggering off the radical clock and generating α-carbonyl radicals. The subsequent photocatalytic oxidation of the resulting α-carbo

SUBMITTER: Liu X 

PROVIDER: S-EPMC12528413 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature