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Photoredox‐Catalyzed Addition of Carbamoyl Radicals to Olefins: A 1,4‐Dihydropyridine Approach

Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C(1)‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO(2)‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene...

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Detalles Bibliográficos
Autores principales: Cardinale, Luana, Konev, Mikhail O., Jacobi von Wangelin, Axel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384035/
https://www.ncbi.nlm.nih.gov/pubmed/32428293
http://dx.doi.org/10.1002/chem.202002410
Descripción
Sumario:Functionalization with C1‐building blocks are key synthetic methods in organic synthesis. The low reactivity of the most abundant C(1)‐molecule, carbon dioxide, makes alternative carboxylation reactions with CO(2)‐surrogates especially important. We report a photoredox‐catalyzed protocol for alkene carbamoylations. Readily accessible 4‐carboxamido‐Hantzsch esters serve as convenient starting materials that generate carbamoyl radicals upon visible light‐mediated single‐electron transfer. Addition to various alkenes proceeded with high levels of regio‐ and chemoselectivity.