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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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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
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author Gevorgyan, Ashot
Obst, Marc F.
Guttormsen, Yngve
Maseras, Feliu
Hopmann, Kathrin H.
Bayer, Annette
author_facet Gevorgyan, Ashot
Obst, Marc F.
Guttormsen, Yngve
Maseras, Feliu
Hopmann, Kathrin H.
Bayer, Annette
author_sort Gevorgyan, Ashot
collection PubMed
description 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.
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spelling pubmed-69911742020-02-13 Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights Gevorgyan, Ashot Obst, Marc F. Guttormsen, Yngve Maseras, Feliu Hopmann, Kathrin H. Bayer, Annette Chem Sci Chemistry 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. Royal Society of Chemistry 2019-09-11 /pmc/articles/PMC6991174/ /pubmed/32055361 http://dx.doi.org/10.1039/c9sc02467k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Gevorgyan, Ashot
Obst, Marc F.
Guttormsen, Yngve
Maseras, Feliu
Hopmann, Kathrin H.
Bayer, Annette
Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title_full Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title_fullStr Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title_full_unstemmed Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title_short Caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
title_sort caesium fluoride-mediated hydrocarboxylation of alkenes and allenes: scope and mechanistic insights
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6991174/
https://www.ncbi.nlm.nih.gov/pubmed/32055361
http://dx.doi.org/10.1039/c9sc02467k
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