Site-Selective C(sp3)-H Alkenylation Using Decatungstate Anion as Photocatalyst

Yi Ting Wang; Yi Lun Shih; Yen Ku Wu; Ilhyong Ryu

doi:10.1002/adsc.202101374

Site-Selective C(sp³)-H Alkenylation Using Decatungstate Anion as Photocatalyst

Yi Ting Wang, Yi Lun Shih, Yen Ku Wu, Ilhyong Ryu^*

^*Corresponding author for this work

Department of Applied Chemistry

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

1 Scopus citations

Abstract

Site-selective C(sp³)-H alkenylation was achieved under photo-irradiation in the presence of a catalytic amount of decatungstate anion, W₁₀O₃₂⁴⁻. In this reaction, the radical addition/β-scission sequence is successfully combined with photocatalytic C(sp³)-H functionalization. The reaction using weaker C−H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C−H bond, and a decatungstate anion participated in a chain-repairing step. (Figure presented.).

Original language	English
Pages (from-to)	1039-1043
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	5
DOIs	https://doi.org/10.1002/adsc.202101374
State	Published - 1 Mar 2022

Keywords

1,2-bis(sulfonyl)ethylene
C(sp)-H alkenylation
benzenesulfonyl radical
decatungstate anion
photocatalyst

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10.1002/adsc.202101374

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title = "Site-Selective C(sp3)-H Alkenylation Using Decatungstate Anion as Photocatalyst",

abstract = "Site-selective C(sp3)-H alkenylation was achieved under photo-irradiation in the presence of a catalytic amount of decatungstate anion, W10O324−. In this reaction, the radical addition/β-scission sequence is successfully combined with photocatalytic C(sp3)-H functionalization. The reaction using weaker C−H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C−H bond, and a decatungstate anion participated in a chain-repairing step. (Figure presented.).",

keywords = "1,2-bis(sulfonyl)ethylene, C(sp)-H alkenylation, benzenesulfonyl radical, decatungstate anion, photocatalyst",

author = "Wang, {Yi Ting} and Shih, {Yi Lun} and Wu, {Yen Ku} and Ilhyong Ryu",

note = "Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH",

year = "2022",

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doi = "10.1002/adsc.202101374",

language = "English",

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T1 - Site-Selective C(sp3)-H Alkenylation Using Decatungstate Anion as Photocatalyst

AU - Wang, Yi Ting

AU - Shih, Yi Lun

AU - Wu, Yen Ku

AU - Ryu, Ilhyong

PY - 2022/3/1

Y1 - 2022/3/1

N2 - Site-selective C(sp3)-H alkenylation was achieved under photo-irradiation in the presence of a catalytic amount of decatungstate anion, W10O324−. In this reaction, the radical addition/β-scission sequence is successfully combined with photocatalytic C(sp3)-H functionalization. The reaction using weaker C−H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C−H bond, and a decatungstate anion participated in a chain-repairing step. (Figure presented.).

AB - Site-selective C(sp3)-H alkenylation was achieved under photo-irradiation in the presence of a catalytic amount of decatungstate anion, W10O324−. In this reaction, the radical addition/β-scission sequence is successfully combined with photocatalytic C(sp3)-H functionalization. The reaction using weaker C−H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C−H bond, and a decatungstate anion participated in a chain-repairing step. (Figure presented.).

KW - 1,2-bis(sulfonyl)ethylene

KW - C(sp)-H alkenylation

KW - benzenesulfonyl radical

KW - decatungstate anion

KW - photocatalyst

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U2 - 10.1002/adsc.202101374

DO - 10.1002/adsc.202101374

M3 - Article

AN - SCOPUS:85123897812

VL - 364

SP - 1039

EP - 1043

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 5

ER -

Site-Selective C(sp³)-H Alkenylation Using Decatungstate Anion as Photocatalyst

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