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NaI/PPh(3)-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles
A practical NaI/PPh(3)-catalyzed decarboxylative radical cascade cyclization of N-arylacrylamides with redox-active esters is described, which is mediated by visible light irradiation. A wide range of substrates bearing different substituents and derived from ubiquitous carboxylic acids, including α...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9874234/ https://www.ncbi.nlm.nih.gov/pubmed/36741816 http://dx.doi.org/10.3762/bjoc.19.5 |
Sumario: | A practical NaI/PPh(3)-catalyzed decarboxylative radical cascade cyclization of N-arylacrylamides with redox-active esters is described, which is mediated by visible light irradiation. A wide range of substrates bearing different substituents and derived from ubiquitous carboxylic acids, including α-amino acids, were synthesized and examined under this very mild, efficient, and cost effective transition-metal-free synthetic method. These afforded various functionalized oxindoles featuring a C3 quaternary stereogenic center. Mechanistic experiments suggest a radical mechanism. |
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