Gold(I)‐Catalyzed Nucleophilic Allylation of Azinium Ions with Allylboronates

Gold(I)‐catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4‐dihydropyridines and 1,4‐dihydroquin...

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Detalles Bibliográficos
Autores principales: O'Brien, Luke, Argent, Stephen P., Ermanis, Kristaps, Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9314030/
https://www.ncbi.nlm.nih.gov/pubmed/35239987
http://dx.doi.org/10.1002/anie.202202305
Descripción
Sumario:Gold(I)‐catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates are reported. The reactions are completely selective with respect to the site of the azinium ion that is attacked, to give various functionalized 1,4‐dihydropyridines and 1,4‐dihydroquinolines. Evidence suggests that the reactions proceed through nucleophilic allylgold(I) intermediates formed by transmetalation from allylboronates. Density functional theory (DFT) calculations provided mechanistic insight.

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