![Author ORCID: We display the ORCID iD icon alongside authors names on our website to acknowledge that the ORCiD has been authenticated when entered by the user. To view the users ORCiD record click the icon. [opens in a new tab]](https://chemrxiv.org/engage/assets/public/chemrxiv/images/logos/orcid.png)
Abstract
We report a light-promoted hydroselenation of alkenes with high anti-Markovnikov selectivity. Spectroscopic, kinetic, and computational mechanistic studies indicate that blue light activates an aryl diselenide to generate a seleno radical; this radical adds into an alkene to form a β-seleno carbon radical. Subsequent hydrogen atom transfer (HAT) 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.
Supplementary materials
Title
Supplementary Information for: Hydroselenation of Simple Olefins: Elucidating the β-Selenide Radical Effect
Description
Includes general procedures and characterization data for synthesis of starting materials, anti-Markovnikov hydroselenation, sensitivity assessment, mechanistic studies, and computational studies.
Actions
