Deng, YongmingZhang, JasonBankhead, BradleyMarkham, Jonathan P.Zeller, Matthias2023-05-052023-05-052021-05Deng, Y., Zhang, J., Bankhead, B., Markham, J. P., & Zeller, M. (2021). Photoinduced oxidative cyclopropanation of ene-ynamides: Synthesis of 3-aza[n.1.0]bicycles via vinyl radicals. Chemical Communications, 57(43), 5254–5257. https://doi.org/10.1039/d1cc02016a1359-7345, 1364-548Xhttps://hdl.handle.net/1805/32832The first photoinduced synthesis of polyfunctionalized 3-aza[n.1.0]bicycles from readily available ene-ynamides and 2,6-lutidine N-oxide using an organic acridinium photocatalyst is reported. Applying a photocatalytic strategy to the reactive distonic cation vinyl radical intermediate from ynamide, a series of bio-valuable 3-azabicycles, including diverse 3-azabicyclio[4.1.0]heptanes and 3-azabicyclo[5.1.0]octanes that are challenging to accomplish using traditional methods, have been successfully synthesized in good to high yields under mild and metal-free conditions. Mechanistic studies are consistent with the photocatalyzed single-electron oxidation of ene-ynamide and the intermediacy of a putative cationic vinyl radical in this transformation. Importantly, this strategy provides new access to the development of photocatalytic vinyl radical cascades for the synthesis of structurally sophisticated substrates.en-USPublisher PolicyAlkynesAza CompoundsMolecular StructurePhotochemical ProcessesArticle