Hydroselenation of olefins: elucidating the β-selenium effect

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

doi:10.1039/d4sc05766j

Hydroselenation of olefins: elucidating the β-selenium effect

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

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.

Original language	English
Pages (from-to)	20523-20533
Number of pages	11
Journal	Chemical Science
Volume	15
Issue number	48
DOIs	https://doi.org/10.1039/d4sc05766j
Publication status	Published - 25 Nov 2024
Externally published	Yes

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title = "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.",

author = "Phun, \{Gabriel S.\} and Slocumb, \{Hannah S.\} and Ruud, \{Kirsten J.\} and Shaozhen Nie and Cheyenne Antonio and Filipp Furche and Dong, \{Vy M.\} and Yang, \{Xiao Hui\}",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

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doi = "10.1039/d4sc05766j",

language = "English",

volume = "15",

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TY - JOUR

T1 - Hydroselenation of olefins

T2 - elucidating the β-selenium effect

AU - Phun, Gabriel S.

AU - Slocumb, Hannah S.

AU - Ruud, Kirsten J.

AU - Nie, Shaozhen

AU - Antonio, Cheyenne

AU - Furche, Filipp

AU - Dong, Vy M.

AU - Yang, Xiao Hui

PY - 2024/11/25

Y1 - 2024/11/25

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85210124557

U2 - 10.1039/d4sc05766j

DO - 10.1039/d4sc05766j

M3 - Article

AN - SCOPUS:85210124557

SN - 2041-6520

VL - 15

SP - 20523

EP - 20533

JO - Chemical Science

JF - Chemical Science

IS - 48

ER -

Hydroselenation of olefins: elucidating the β-selenium effect

Abstract

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