ArticleChemical science2017
Mechanistic analysis of a copper-catalyzed C-H oxidative cyclization of carboxylic acids.
Article in Chemical science, 2017. 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, 41 citations in OpenAlex.
- Room-Temperature Oxidative Cyclization of Carboxylic Acids Promoted by Copper(II) Trifluoromethanesulfonate and Selectfluor.The Journal of organic chemistry · 2026Article
- Mild and efficient coupling reactions enabled byCatalysis science & technology · 2026Article
- Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor.The Journal of organic chemistry · 2023Article
- Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.Journal of the American Chemical Society · 2023Article
- Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes.The Journal of organic chemistry · 2023Article
- Copper-catalysed benzylic C-H coupling with alcohols via radical relay enabled by redox buffering.Nature catalysis · 2020Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We recently reported that carboxylic acids can be oxidized to lactone products by potassium persulfate and catalytic copper acetate. Here, we unravel the mechanism for this C-H functionalization reaction using desorption electrospray ionization, online electrospray ionization, and tandem mass spectrometry. Our findings suggest that electron transfer from a transient benzylic radical intermediate reduces Cu(ii) to Cu(i), which is then re-oxidized to Cu(ii) in the catalytic cycle. The resulting benzylic carbocation is trapped by the pendant carboxylate group to give the lactone product. Formation of the putative benzylic carbocation is supported by Hammett analysis. The proposed mechanism for this copper-catalyzed oxidative cyclization process differs from earlier reports of analogous reactions, which posit a substrate carboxylate radical as the reactive oxidant.
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Registered trials
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