ArticleScience advances2023
Olefination of carbonyls with alkenes enabled by electrophotocatalytic generation of distonic radical cations.
Article in Science advances, 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.
- General Alkene 1,2-Journal of the American Chemical Society · 2024Article
- A Unified Synthesis of Diazenes from Primary Amines Using a SuFEx/Electrochemistry Strategy.Organic letters · 2024Article
- Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations.Beilstein journal of organic chemistry · 2024Review
- Ketyl Radical Coupling Enabled by Polycyclic Aromatic Hydrocarbon Electrophotocatalysts.Journal of the American Chemical Society · 2023Article
- Shining Fresh Light on Complex Photoredox Mechanisms through Isolation of Intermediate Radical Anions.ACS catalysis · 2023Article
- Cross-Coupling of Amines via Photocatalytic Denitrogenation of In Situ Generated Diazenes.Journal of the American Chemical Society · 2023Article
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Authors and funding
2 authors.
Funding
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Abstract
The conversion of carbonyls to olefins is a transformation of great importance for complex molecule synthesis. Standard methods use stoichiometric reagents that have poor atom economy and require strongly basic conditions, which limit their functional group compatibility. An ideal solution would be to catalytically olefinate carbonyls under nonbasic conditions using simple and widely available alkenes, yet no such broadly applicable reaction is known. Here, we demonstrate a tandem electrochemical/electrophotocatalytic reaction to olefinate aldehydes and ketones with a broad range of unactivated alkenes. This method involves the oxidation-induced denitrogenation of cyclic diazenes to form 1,3-distonic radical cations that rearrange to yield the olefin products. This olefination reaction is enabled by an electrophotocatalyst that inhibits back-electron transfer to the radical cation intermediate, thus allowing for the selective formation of olefin products. The method is compatible with a wide range of aldehydes, ketones, and alkene partners.
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Registered trials
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