Hydroselenation of olefins: elucidating the β-selenium effect
Gabriel S Phun1, Hannah S Slocumb1, Kirsten J Ruud1
1Department of Chemistry, University of California Irvine California 92697 USA filipp.furche@uci.edu dongv@uci.edu.
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.
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