| Autor: |
Yongming, Deng, Jason, Zhang, Bradley, Bankhead, Jonathan P, Markham, Matthias, Zeller |
| Rok vydání: |
2021 |
| Předmět: |
|
| Zdroj: |
Chemical communications (Cambridge, England). 57(43) |
| ISSN: |
1364-548X |
| Popis: |
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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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