Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

He Huang; Zack M. Strater; Tristan H. Lambert

doi:10.1021/jacs.9b11472

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

He Huang
, Zack M. Strater
, Tristan H. Lambert^*

^*此作品的通讯作者

科研成果: 期刊稿件 › 文章 › 同行评审

173 引用（Scopus）

摘要

The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

源语言	英语
页（从-至）	1698-1703
页数	6
期刊	Journal of the American Chemical Society
卷	142
期	4
DOI	https://doi.org/10.1021/jacs.9b11472
出版状态	已出版 - 29 1月 2020
已对外发布	是

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abstract = "The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.",

author = "He Huang and Strater, \{Zack M.\} and Lambert, \{Tristan H.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/jacs.9b11472",

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AU - Huang, He

AU - Strater, Zack M.

AU - Lambert, Tristan H.

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Y1 - 2020/1/29

N2 - The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

AB - The highly regioselective electrophotocatalytic C-H functionalization of ethers is described. These reactions are catalyzed by a trisaminocyclopropenium (TAC) ion at mild electrochemical potential with visible light irradiation. Ethers undergo oxidant-free coupling with isoquinolines, alkenes, alkynes, pyrazoles, and purines with typically high regioselectivity for the less-hindered α-position. The reaction is proposed to operate via hydrogen atom transfer (HAT) from the substrate to the photoexcited TAC radical dication, thus demonstrating a new reactivity mode for this electrophotocatalyst.

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DO - 10.1021/jacs.9b11472

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 4

ER -

Electrophotocatalytic C-H Functionalization of Ethers with High Regioselectivity

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