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.
Authors
- Zhiqiang Zhu (ORCID: https://orcid.org/0000-0003-4915-9357)
- Xu Zhenzhen (ORCID: https://orcid.org/0009-0000-1829-6434)
- Wenyi Zhang (ORCID: https://orcid.org/0000-0001-5530-4210)
- Qing Li (ORCID: https://orcid.org/0000-0003-4807-030X)
- Xiao‐Long Huang (ORCID: https://orcid.org/0000-0002-3138-986X)
- H. Surya Prakash Rao (ORCID: https://orcid.org/0000-0003-0816-0116)
Institutions
- Ingenierie des Materiaux polymeres (FR)
- East China University of Technology (CN)
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
Funders
- Natural Science Foundation of Jiangxi Province