The vinylogous Catellani reaction: a combined computational and experimental study

In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed...

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Detalles Bibliográficos
Autores principales: Yamamoto, Y., Murayama, T., Jiang, J., Yasui, T., Shibuya, M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5885779/
https://www.ncbi.nlm.nih.gov/pubmed/29675164
http://dx.doi.org/10.1039/c7sc04265e
Descripción
Sumario:In the presence of 5 mol% Pd(OAc)(2), 1 equiv. of norbornene, and K(2)CO(3), the reaction of 4-iodo-2-quinolones with tertiary o-bromobenzylic alcohols produced the desired benzopyran-fused 2-quinolones in moderate to high yields. A Catellani-type mechanism involving vinylic C–H cleavage is proposed based on the results of control experiments and density functional theory calculations.

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