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

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

Publication History

Received: 16 April 2021

Accepted after revision: 25 May 2021

Article published online:
30 July 2021

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