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Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights

A caesium fluoride-mediated hydrocarboxylation of olefins is disclosed that does not rely on precious transition metal catalysts and ligands. The reaction occurs at atmospheric pressures of CO(2) in the presence of 9-BBN as a stoichiometric reductant. Stilbenes, β-substituted styrenes and allenes co...

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Detalles Bibliográficos
Autores principales: Gevorgyan, Ashot, Obst, Marc F., Guttormsen, Yngve, Maseras, Feliu, Hopmann, Kathrin H., Bayer, Annette
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6991174/
https://www.ncbi.nlm.nih.gov/pubmed/32055361
http://dx.doi.org/10.1039/c9sc02467k
Descripción
Sumario:A caesium fluoride-mediated hydrocarboxylation of olefins is disclosed that does not rely on precious transition metal catalysts and ligands. The reaction occurs at atmospheric pressures of CO(2) in the presence of 9-BBN as a stoichiometric reductant. Stilbenes, β-substituted styrenes and allenes could be carboxylated in good yields. The developed methodology can be used for preparation of commercial drugs as well as for gram scale hydrocarboxylation. Computational studies indicate that the reaction occurs via formation of an organocaesium intermediate.