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Photoinduced oxidative cyclopropanation of ene-ynamides: synthesis of 3-aza[ n .1.0]bicycles via vinyl radicals.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2021 May 27; Vol. 57 (43), pp. 5254-5257. - Publication Year :
- 2021
-
Abstract
- 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.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 57
- Issue :
- 43
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 33973595
- Full Text :
- https://doi.org/10.1039/d1cc02016a