Hydroselenation of olefins: elucidating the β-selenium effect.

ABSTRACT: We report a light-promoted hydroselenation of alkenes with high anti-Markovnikov selectivity. Blue light activates an aryl diselenide to generate a seleno radical with subsequent addition into an alkene to form a β-seleno carbon radical. Hydrogen atom transfer (HAT) from the selenol to the carbon radical generates the linear selenide with high selectivity in preference to the branched isomer. These studies reveal a unique β-selenium effect, where a selenide β to a carbon radical imparts high anti-selectivity for radical addition through delocalization of the HAT transition state.

SUBMITTER: Phun GS 

PROVIDER: S-EPMC11586760 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature