ArticleJournal of the American Chemical Society2023
Overcoming the Potential Window-Limited Functional Group Compatibility by Alternating Current Electrolysis.
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 9 papers.
What it found
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Who cites it
9 citing papers in PubMed.
- Floquet States of Chemoselective Alternating Current Electrosynthesis.Journal of the American Chemical Society · 2026Article
- Nanogalvanic cell catalysts: bridging electrochemical and thermal catalysis.National science review · 2026Article
- Applying asymmetric-waveform alternating current in nickel-catalyzed asymmetric reductive cross-coupling.Nature communications · 2026Article
- Electrochemical Oxidation of Aryl Boronic Acids via Fluoride Activation and Alternating Polarity Electrolysis for Aryl C-P Bond Formation.ChemElectroChem · 2025Article
- Origin of Selectivity in Alternating Current-Enabled Partial Reduction of (Hetero)Arenes: A Case Study of Two Consecutive Irreversible Electrochemical Steps.Journal of the American Chemical Society · 2025Article
- Effect of Alternating Polarity in Electrochemical Olefin Hydrocarboxylation.Angewandte Chemie (International ed. in English) · 2025Article
- A General Hydrotrifluoromethylation of Unactivated Olefins Enabled by Voltage-Gated Electrosynthesis.Angewandte Chemie (International ed. in English) · 2025Article
- Electrochemical Generation of Aryl Radicals from Organoboron Reagents Enabled by Pulsed Electrosynthesis.Angewandte Chemie (International ed. in English) · 2024Article
- Revisiting Alternating Current Electrolysis for Organic Synthesis.Current opinion in electrochemistry · 2024Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The functional group compatibility of an electrosynthetic method is typically limited by its potential reaction window. Here, we report that alternating current (AC) electrolysis can overcome such potential window-limited functional group compatibility. Using alkene heterodifunctionalization as a model system, we design and demonstrate a series of AC-driven reactions that add two functional groups sequentially and separately under the cathodic and anodic pulses, including chloro- and bromotrilfuoromethylation as well as chlorosulfonylation. We discovered that the oscillating redox environment during AC electrolysis allows the regeneration of the redox-active functional groups after their oxidation or reduction in the preceding step. As a result, even though redox labile functional groups such as pyrrole, quinone, and aryl thioether fall in the reaction potential window, they are tolerated under AC electrolysis conditions, leading to synthetically useful yields. The cyclic voltammetric study has confirmed that the product yield is limited by the extent of starting material regeneration during the redox cycling. Our findings open a new avenue for improving functional group compatibility in electrosynthesis and show the possibility of predicting the product yield under AC electrolysis from voltammogram features.
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Registered trials
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