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

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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.

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

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Publication details

The article was received on 20 May 2019, accepted on 11 Sep 2019 and first published on 11 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC02467K
Chem. Sci., 2019, Advance Article
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    Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights

    A. Gevorgyan, M. F. Obst, Y. Guttormsen, F. Maseras, K. H. Hopmann and A. Bayer, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC02467K

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