Room Temperature Electro-carboxylation of Styrene and Stilbene Derivatives: A Comparative Study

Alhathlaul, N., Ertekin, Z. and Symes, M. D. (2023) Room Temperature Electro-carboxylation of Styrene and Stilbene Derivatives: A Comparative Study. [Data Collection]

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The use of carbon dioxide as a comparatively cheap, abundant and non-toxic C-1 synthon is a topic of considerable interest and importance. The electrochemical addition of carbon dioxide across carbon-carbon double bonds is one of the more promising of such procedures, offering the possibility to convert a range of alkene substrates to valuable carboxylated products. However, much remains unknown about both the mechanism of reaction and how to influence product specificity during electro-carboxylation of alkenes. Herein, we explore the electrochemical addition of carbon dioxide (1 atm) to a range of olefinic substrates using nickel working electrodes and magnesium anodes at room temperature, producing the mono-substituted carboxylate derivatives preferentially (with no formation of the Markovnikov isomers of these mono-substituted carboxylate derivatives when the starting materials are non-symmetrical). These findings are rationalized using both experimental and computational methods, suggesting that the choice of Ni as a working electrode is critical in determining the reaction outcomes that are observed. Moreover, we also present direct evidence that a pathway whereby the alkene substrates are first reduced at the electrode surface and then react with dissolved CO2 is operating. Together, these results offer the potential for selective access to a range of valuable mono-carboxylic acids via the reduction of the corresponding alkene precursors in the presence of carbon dioxide.

Funding:
College / School: College of Science and Engineering > School of Chemistry
Date Deposited: 30 Oct 2023 11:40
Related resources:
URI: http://researchdata.gla.ac.uk/id/eprint/1520

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Alhathlaul, N., Ertekin, Z. and Symes, M. D. (2023); Room Temperature Electro-carboxylation of Styrene and Stilbene Derivatives: A Comparative Study

University of Glasgow

DOI: 10.5525/gla.researchdata.1520

Retrieved: 2024-02-28

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