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Visible-Light-Induced C–H Cyanoalkylation of Azauracils with Cycloketone Oxime Esters via Catalytic EDA Complex

Xiaolong Huang, Dong‐Liang Zhang, Qing Li, Zongbo Xie, Zhanggao Le, Zhiqiang Zhu

2024Organic Letters45 citationsDOI

Abstract

Photoexcitation electron donor-acceptor (EDA) complexes provide an effective approach to produce radicals under mild conditions, while the catalytic version of EDA complex photoactivation remains scarce. Herein, we report a visible-light-induced organophotocatalytic pathway for the cyanoalkylation of azauracils using inexpensive and readily available 1,4-diazabicyclo[2.2.2]octane (DABCO) as a catalytic electron donor. This synthetic method exhibits exceptional compatibility with various functional groups and presents 34 examples in high yields. The efficient cyanoalkylation offers an environmentally friendly and sustainable route toward enhancing the structural and functional diversity of azauracils.

Topics & Concepts

ChemistryDABCOCatalysisOctanePhotoexcitationOximeCombinatorial chemistryRadicalAcceptorPhotochemistryOrganic chemistryCondensed matter physicsNuclear physicsPhysicsExcited stateRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives