Photoinduced direct C-H cyanoalkylation of azauracils via electron donor-acceptor complex activation

Abstract

Photoinduced C-H functionalization of azauracils predominantly rely on the use of noble metal photocatalysts or synthetically elaborated organic dyes to govern selective reactivity. Herein, we report direct C-H cyanoalkylation of azauracils with cycloketone oxime esters via electron donor-acceptor (EDA) complex photoactivation. The transiently formed chromophoric assembly between azauracils and cycloketone oxime esters plays a pivotal role in enabling intermolecular electron transfer, thereby driving the C-H cyanoalkylation process. Mechanistic studies and density functional theory (DFT) calculations support the proposed EDA complex scenario. This synthetic approach operates under redox-neutral conditions without exogenous photocatalysts and additives, showcasing significant potential for drug design and bioactive molecules synthesis.