Investigation on the Stoichiometry of Carbon Dioxide in Isotope-Exchange Reactions with Phenylacetic Acids

Alex Talbot; Antoine Sallustrau; Amélie Goudet; Frédéric Taran; Davide Audisio

doi:10.1055/s-0040-1720447

Synlett, Table of Contents

Synlett 2022; 33(02): 171-176
DOI: 10.1055/s-0040-1720447

letter

EuCheMS Organic Division Young Investigator Workshop

Investigation on the Stoichiometry of Carbon Dioxide in Isotope-Exchange Reactions with Phenylacetic Acids

Alex Talbot

,

Antoine Sallustrau

,

Amélie Goudet

,

Frédéric Taran

,

Davide Audisio ∗

Abstract

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Abstract

The functionalization of carbon dioxide (CO₂) as a C1 building block has attracted enormous attention. Carboxylation reactions, in particular, are of major interest for applications in isotope labeling. Due to the inexpensive nature of CO₂, information about its stoichiometric use is generally unavailable in the literature. Because of the rarity and limited availability of CO₂ isotopomers, this parameter is of concern for applications in carbon-isotope labeling. We investigated the effects of the stoichiometry of labeled CO₂ on carbon isotope exchange of phenylacetic acids. Both thermal and photocatalytic procedures were studied, providing insight into product outcome and isotope incorporation. Preliminary results on isotope-dilution effects of carbonate bases in photocatalytic carboxylation reactions have also been obtained.

Key words

carbon dioxide - isotope labeling - photoredox catalysis - decarboxylation - carboxylation

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References

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