Visible Light-Induced C–H Alkylation of Azauracils with <i>N</i>-Hydroxyphthalimide Esters via Catalytic EDA Complex

Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C-H alkylation of azauracils with <i>N</i>-hydroxyphthalimide (NHPI) esters facilitated by visible light activation of catalytic electron donor-acceptor (EDA) complexes. Control experiments and density functional theory calculations suggest that the decarboxylative coupling reaction proceeds via a transiently assembled EDA complex between the NHPI ester and NaI in <i>N</i>,<i>N</i>-dimethylacetamide solvent. This synthetic method efficiently applies to primary, secondary, and tertiary NHPI esters under mild, photocatalyst-free, and redox-neutral conditions, achieving high yields of the desired alkylated azauracils.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-13
DOI
https://doi.org/10.1021/acs.joc.4c02177
Citations
15
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
14.04

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article

Visible Light-Induced C–H Alkylation of Azauracils with N-Hydroxyphthalimide Esters via Catalytic EDA Complex

Zhiqiang Zhu, Xu Zhenzhen, Wenyi Zhang, Qing Li et al.
15 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
14.04
article

Visible Light-Induced C–H Alkylation of Azauracils with N-Hydroxyphthalimide Esters via Catalytic EDA Complex

Zhiqiang Zhu, Xu Zhenzhen, Wenyi Zhang, Qing Li, Xiao‐Long Huang, H. Surya Prakash Rao
article en
15 citations

Abstract

Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C-H alkylation of azauracils with <i>N</i>-hydroxyphthalimide (NHPI) esters facilitated by visible light activation of catalytic electron donor-acceptor (EDA) complexes. Control experiments and density functional theory calculations suggest that the decarboxylative coupling reaction proceeds via a transiently assembled EDA complex between the NHPI ester and NaI in <i>N</i>,<i>N</i>-dimethylacetamide solvent. This synthetic method efficiently applies to primary, secondary, and tertiary NHPI esters under mild, photocatalyst-free, and redox-neutral conditions, achieving high yields of the desired alkylated azauracils.

The Journal of Organic ChemistryVol. 90(8)
Ingenierie des Materiaux polymeres (FR), East China University of Technology (CN)
Natural Science Foundation of Jiangxi Province
Openalex Percentile: Top 1%
Radical Photochemical Reactions
14.04
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