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

作者：Zhiqiang Zhu, Wenyi Zhang, Xiao‐Long Huang, Qing Li, Xu Zhenzhen, H. Surya Prakash Rao · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.4c02177 · 被引用次数：24 · 研究领域：Radical Photochemical Reactions、Catalytic C–H Functionalization Methods、Oxidative Organic Chemistry Reactions

Herein, we report sodium iodide (NaI)-catalyzed decarboxylative C–H alkylation of azauracils with N -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 N, N -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.