Access to Functionalized E‑Allylsilanes and E‑Alkenylsilanes through Visible-Light-Driven Radical Hydrosilylation of Mono- and Disubstituted Allenes

Access to Functionalized E‑Allylsilanes and E‑Alkenylsilanes through Visible-Light-Driven Radical Hydrosilylation of Mono- and Disubstituted Allenes

A visible-light-driven radical hydrosilylation of allene has been achieved by using eosin Y as the photocatalyst, with thiol and base as additives. Depending on allenes, two types of adducts with E-selectivity were obtained. It was demonstrated that monosubstituted nonarylated allenes reacted to giv...

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Veröffentlicht in:Organic letters 2019-12, Vol.21 (24), p.9836-9840
Hauptverfasser: Cai, Yanyao, Zhao, Wenxuan, Wang, Shaozhong, Liang, Yong, Yao, Zhu-Jun
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container_end_page 9840
container_issue 24
container_start_page 9836
container_title Organic letters
container_volume 21
creator Cai, Yanyao
Zhao, Wenxuan
Wang, Shaozhong
Liang, Yong
Yao, Zhu-Jun
description A visible-light-driven radical hydrosilylation of allene has been achieved by using eosin Y as the photocatalyst, with thiol and base as additives. Depending on allenes, two types of adducts with E-selectivity were obtained. It was demonstrated that monosubstituted nonarylated allenes reacted to give linear E-allylsilanes, while 1,3-disubstituted electron-deficient allenes afforded E-alkenylsilanes. A radical mechanism was proposed to account for the chemo-, regio-, and stereoselective formation of these functionalized silicon-containing compounds.
doi_str_mv 10.1021/acs.orglett.9b03679
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title Access to Functionalized E‑Allylsilanes and E‑Alkenylsilanes through Visible-Light-Driven Radical Hydrosilylation of Mono- and Disubstituted Allenes
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