Photocatalyst-Free Transformation of C(sp<sup>3</sup>)–H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer

Herein, a direct transformation of aliphatic C-H bonds to oxime ethers has been developed via light-promoted hydrogen atom transfer (HAT) in the absence of a photocatalyst. Singlet oxygen and chlorine radical are complementary C(sp<sup>3</sup>)-H bond cleaving agents in this reaction, enabling the extraction of hydrogen atoms from a diverse range of compounds, like cycloalkanes, ethers, amines, amides, and cyclic sulfides. This method excels in transforming common aliphatic C-H bonds into valuable oxime ethers featuring abundant chemical feedstocks, good functional group tolerance, and catalyst free conditions.

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Publication Details

Journal
Organic Letters
Published
2024-10-22
DOI
https://doi.org/10.1021/acs.orglett.4c03653
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.50

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article

Photocatalyst-Free Transformation of C(sp3)–H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer

Xiaole Han, Wei Yi, Lijing Li, Xiao‐Qiang Hu et al.
6 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.50
article

Photocatalyst-Free Transformation of C(sp3)–H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer

Xiaole Han, Wei Yi, Lijing Li, Xiao‐Qiang Hu, Xuehong Min, Yulian Zhao
article en
6 citations

Abstract

Herein, a direct transformation of aliphatic C-H bonds to oxime ethers has been developed via light-promoted hydrogen atom transfer (HAT) in the absence of a photocatalyst. Singlet oxygen and chlorine radical are complementary C(sp<sup>3</sup>)-H bond cleaving agents in this reaction, enabling the extraction of hydrogen atoms from a diverse range of compounds, like cycloalkanes, ethers, amines, amides, and cyclic sulfides. This method excels in transforming common aliphatic C-H bonds into valuable oxime ethers featuring abundant chemical feedstocks, good functional group tolerance, and catalyst free conditions.

Organic LettersVol. 26(43)
Minzu University of China (CN), Wuhan Business University (CN), Horse Hospital (GB)
National Natural Science Foundation of China, Natural Science Foundation of Hubei Province, Wuhan Business University, South-Central University for Nationalities
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
1.50
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Photocatalyst-Free Transformation of C(sp<sup>3</sup>)–H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer — Xiaole Han, Wei Yi, et al. · Organic Letters (2024) | TGRS Research Map | TGRS