Hydroselenation of olefins: elucidating the β-selenium effect

Phun, Gabriel S.; Slocumb, Hannah S.; Ruud, Kirsten J.; Nie, Shaozhen; Antonio, Cheyenne; Furche, Filipp; Dong, Vy M.; Yang, Xiao-Hui

doi:10.1039/D4SC05766J

Title: Hydroselenation of olefins: elucidating the β-selenium effect

Journal Article · 24 November 2024 · Chemical Science

DOI: https://doi.org/10.1039/D4SC05766J · OSTI ID:2478738

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^[1]; Nie, Shaozhen ^[2]; Antonio, Cheyenne ^[3];

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Univ. of California, Irvine, CA (United States)
Glaxo-Smith-Kline, Collegeville, PA (United States)
Univ. of California, San Francisco, CA (United States)
Beijing Institute of Technology (China); Nankai Univ., Tianjin (China)

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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Research Organization:: Univ. of California, Irvine, CA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0025405

OSTI ID:: 2478738

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 48 Vol. 15; ISSN 2041-6539; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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