Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates

Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl(2)(PPh(3))(2), ZnCl(2), Et(3)N and Zn in THF. Both steric and electronic factors played a role in the outcom...

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Detalles Bibliográficos
Autores principales: Edmunds, Michael, Raheem, Mohammed Abdul, Boutin, Rebecca, Tait, Katrina, Tam, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778517/
https://www.ncbi.nlm.nih.gov/pubmed/26977182
http://dx.doi.org/10.3762/bjoc.12.25
Descripción
Sumario:Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl(2)(PPh(3))(2), ZnCl(2), Et(3)N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained.

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