ArticleJournal of the American Chemical Society2023
Toward Improving the Selectivity of Organic Halide Electrocarboxylation with Mechanistically Informed Solvent Selection.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Competing pathways in electrocarboxylation on copper electrodes: defining reactivity regimes through substrate activation and COFaraday discussions · 2026Article
- Unlocking Interfacial Catalytic Halogen Atom Transfer at Ag Electrodes with Brønsted Acids.Journal of the American Chemical Society · 2026Article
- Solvent Sustainability in Drug Discovery: Where Are We Now, and How Can We Improve?Journal of medicinal chemistry · 2025Review
- Surfactant-enhanced CuNature communications · 2025Article
- Repurposing First-Row Transition Metal Carbon Dioxide Reduction Electrocatalysts for Electrochemical Carboxylation of Benzyl Chloride.ACS organic & inorganic Au · 2024Article
- Fine tuning of electrosynthesis pathways by modulation of the electrolyte solvation structure.Chemical science · 2023Review
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The use of a liquid electrolyte is nearly ubiquitous in electrosynthetic systems and can have a significant impact on the selectivity and efficiency of electrochemical reactions. Solvent selection is thus a key step during optimization, yet this selection process usually involves trial-and-error. As a step toward more rational solvent selection, this work examines how the electrolyte solvent impacts the selectivity of electrocarboxylation of organic halides. For the carboxylation of a model alkyl bromide, hydrogenolysis is the primary side reaction. Isotope-labeling studies indicate the hydrogen atom in the hydrogenolysis product comes solely from the aprotic electrolyte solvent. Further mechanistic studies reveal that under synthetically relevant electrocarboxylation conditions, the hydrogenolysis product is formed via deprotonation of the solvent. Guided by these mechanistic findings, a simple computational descriptor based on the free energy to deprotonate a solvent molecule was shown to correlate strongly with carboxylation selectivity, overcoming limitations of traditional solvent descriptors such as p
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Registered trials
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