Issue 43, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
20 May 2019
Accepted
11 Sep 2019
First published
11 Sep 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 10072-10078

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, 10, 10072 DOI: 10.1039/C9SC02467K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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