Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
Ashot Gevorgyan1, Marc F Obst2, Yngve Guttormsen1
1Department of Chemistry , UiT The Arctic University of Norway , Norway .
Abstract:
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 CO2 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.
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