1433141-34-4Relevant articles and documents
Photoinduced oxidative cyclopropanation of ene-ynamides: Synthesis of 3-aza[: N.1.0]bicycles via vinyl radicals
Deng, Yongming,Zhang, Jason,Bankhead, Bradley,Markham, Jonathan P.,Zeller, Matthias
supporting information, p. 5254 - 5257 (2021/06/06)
The 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. This journal is
