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

Abstract

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.