Photoinduced oxidative cyclopropanation of ene-ynamides: synthesis of 3-aza[n.1.0]bicycles via vinyl radicals

Autor:	Matthias Zeller, Bradley Bankhead, Jonathan P. Markham, Yongming Deng, Jason Zhang
Rok vydání:	2021
Předmět:	Cyclopropanation Chemistry Radical Metals and Alloys Cationic polymerization General Chemistry Oxidative phosphorylation Combinatorial chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials Materials Chemistry Ceramics and Composites Photocatalysis Ene reaction
Zdroj:	Chemical Communications. 57:5254-5257
ISSN:	1364-548X 1359-7345
DOI:	10.1039/d1cc02016a
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
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