Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Liu, Dan, Zhao, Yue, Patureau, Frederic W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
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
Descripción
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.