Photoredox-Catalyzed Deoxygenative C–H Alkylation of Azauracils via Xanthate-Activated Alcohols

A visible-light-driven method has been developed for the deoxygenative alkylation of azauracils with alcohols, utilizing xanthate salts as alkylation precursors in the presence of tricyclohexylphosphine. This approach features mild conditions, high step efficiency, and a broad substrate scope, enabling the use of primary, secondary and tertiary alcohols as alkylating agents. Additionally, mechanistic investigations suggest a photoredox-mediated radical pathway that involves xanthate intermediates, thereby enhancing the reaction selectivity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-09-20
DOI
https://doi.org/10.1021/acs.joc.5c02047
Citations
2
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.87
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article

Photoredox-Catalyzed Deoxygenative C–H Alkylation of Azauracils via Xanthate-Activated Alcohols

Yuntao Xia, Jinwei Yuan, Liangru Yang, Yongmei Xiao et al.
2 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
1.87
article

Photoredox-Catalyzed Deoxygenative C–H Alkylation of Azauracils via Xanthate-Activated Alcohols

Yuntao Xia, Jinwei Yuan, Liangru Yang, Yongmei Xiao, Ling Cui, Lili Wang, Dongliang Xing, Lingbo Qu
article en
2 citations

Abstract

A visible-light-driven method has been developed for the deoxygenative alkylation of azauracils with alcohols, utilizing xanthate salts as alkylation precursors in the presence of tricyclohexylphosphine. This approach features mild conditions, high step efficiency, and a broad substrate scope, enabling the use of primary, secondary and tertiary alcohols as alkylating agents. Additionally, mechanistic investigations suggest a photoredox-mediated radical pathway that involves xanthate intermediates, thereby enhancing the reaction selectivity.

The Journal of Organic ChemistryVol. 90(39)
Henan University of Technology (CN), Henan Academy of Sciences (CN), Fifth Affiliated Hospital of Zhengzhou University (CN)
Openalex Percentile: Top 13%
Radical Photochemical Reactions
1.87
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