ArticleScience advances2017
A remote C-C bond cleavage-enabled skeletal reorganization: Access to medium-/large-sized cyclic alkenes.
Article in Science advances, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Successive Ring Expansion Strategies for the Synthesis of Macrocycles and Medium-Sized Rings.Chemical reviews · 2026Article
- Remote difunctionalization of alkenes through a photocatalytically triggered radical clock and α-carbonyl carbocation generation.Communications chemistry · 2025Article
- Radical-triggered translocation of C-C double bond and functional group.Nature chemistry · 2024Article
- A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions.Journal of the American Chemical Society · 2024Article
- Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce-Smiles rearrangement.Nature communications · 2022Article
- Skeletal reorganization divergence of N-sulfonyl ynamides.Nature communications · 2020Article
- Anodic oxidation triggered divergent 1,2- and 1,4-group transfer reactions of β-hydroxycarboxylic acids enabled by electrochemical regulation.Chemical science · 2020Article
- A happy medium: the synthesis of medicinally important medium-sized ringsChemical science · 2020Review
- Article
- Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moietyChemical science · 2018Article
- Alkene 1,2-Difunctionalization by Radical Alkenyl Migration.Angewandte Chemie (International ed. in English) · 2018Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Although great success has been achieved in selective C-C bond cleavage via the intramolecular radical remote migration process of several carbon-based groups, the development of the radical-based remote vinyl migration process remains a formidable challenge because of the energetically unfavorable process. To address this problem, we report here, for the first time, a novel C-C bond reorganization strategy via an unprecedented radical 1,3-, 1,4-, or 1,5-vinyl migration triggered by various types of fluoroalkylation of alkenes for the efficient realization of 1,2-fluoroalkylalkenylation reaction. This strategy provides an expedient and broadly applicable platform to access skeletally and functionally diverse fluoroalkyl-containing medium- and large-sized cyclic alkenes with excellent chemo-, regio-, and stereoselectivity. The broad substrate scope, which covers distinctly electron-neutral or electron-deficient alkenyl migrating groups and various fluoroalkyl radical precursors, the excellent functional group tolerance, the remarkable selectivity, and the operational simplicity, as well as versatile transformations of the products, make this approach practical and attractive.
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Registered trials
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