ArticleTetrahedron2017
Copper-catalyzed [1,2]-rearrangements of allylic iodides and aryl α-diazoacetates.
Article in Tetrahedron, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- The Catalytic Enantioselective Sommelet-Hauser Rearrangement.Journal of the American Chemical Society · 2026Article
- Site-Selective Carbonylation of Azetidines via Copper-Catalyzed Difluorocarbene Insertion.Angewandte Chemie (International ed. in English) · 2025Article
- Record-High Efficiency Blue-Green Cationic Ir(III) Complexes for Light-Emitting Electrochemical Cells with EQE Approaching 40.Inorganic chemistry · 2025Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Catalytic rearrangements of onium ylides in aromatic systems.Organic & biomolecular chemistry · 2022Review
- Enantioselective [1,2]-Stevens rearrangement of thiosulfonates to construct dithio-substituted quaternary carbon centers.Chemical science · 2022Article
- Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides.Journal of the American Chemical Society · 2021Article
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3 authors.
Funding
Abstract
The [1,2]- and [2,3]-rearrangements of iodonium ylides are synthetically useful reactions for the generation of functionalized α-iodoesters. Allylic iodides are coupled with α-diazoesters in the presence of a copper catalyst and a ligand to generate iodonium ylides, which undergo metal-mediated rearrangements. By fine-tuning the structure of the ligand, we have reversed the regioselectivity of copper-catalyzed reactions of iodonium ylides from [2,3]- to [1,2]-rearrangements with the use of alternate bipyridine ligands. The preference for [1,2]-rearrangements was further improved by using bulky aryl α-diazoester substrates. Several α-iodoesters with a diverse range of functional groups were generated in good yields (up to 88% yield) and high regioselectivities (up to >95:5 regioisomeric ratio). A deuterium-labeled substrate was utilized to gain insight into the mechanism of the reaction.
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