Visible-Light Induced Etherification of C(sp<sup>3</sup>)–H Bonds with Phenols

The visible-light induced cross-dehydrogenative coupling of C(sp<sup>3</sup>)-H bonds with phenols using BrCCl<sub>3</sub> to give aryl alkyl ethers has been achieved under transition-metal- and photocatalyst-free conditions. This operationally simple and mild protocol has a broad substrate scope, and was applied to the modification of drug molecules and on a gram-scale synthesis. The phenolate ion functions as both a substrate and photosensitizer, and BrCCl<sub>3</sub> serves as the oxidant and hydrogen atom transfer (HAT) agent.

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Publication Details

Journal
Organic Letters
Published
2025-05-03
DOI
https://doi.org/10.1021/acs.orglett.5c01018
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Visible-Light Induced Etherification of C(sp3)–H Bonds with Phenols

Hong‐Xi Li, Zelin Zhao, David J. Young, Xinhua Lu et al.
2 citations
Organic Letters
Radical Photochemical Reactions
1.87
article

Visible-Light Induced Etherification of C(sp3)–H Bonds with Phenols

Hong‐Xi Li, Zelin Zhao, David J. Young, Xinhua Lu, Zhi‐Gang Ren, Xin Fang, Jing Qian
article en
2 citations

Abstract

The visible-light induced cross-dehydrogenative coupling of C(sp<sup>3</sup>)-H bonds with phenols using BrCCl<sub>3</sub> to give aryl alkyl ethers has been achieved under transition-metal- and photocatalyst-free conditions. This operationally simple and mild protocol has a broad substrate scope, and was applied to the modification of drug molecules and on a gram-scale synthesis. The phenolate ion functions as both a substrate and photosensitizer, and BrCCl<sub>3</sub> serves as the oxidant and hydrogen atom transfer (HAT) agent.

Organic LettersVol. 27(19)
University of Glasgow (GB)
National Natural Science Foundation of China, Priority Academic Program Development of Jiangsu Higher Education Institutions
Zero hunger
Openalex Percentile: Top 16%
Radical Photochemical Reactions
1.87
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Visible-Light Induced Etherification of C(sp<sup>3</sup>)–H Bonds with Phenols — Hong‐Xi Li, Zelin Zhao, et al. · Organic Letters (2025) | TGRS Research Map | TGRS