ArticleNature communications2024
Observation of unusual outer-sphere mechanism using simple alkenes as nucleophiles in allylation chemistry.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- AgBFChemical science · 2026Article
- Rhodium-catalyzed atroposelective C-H fluoroallylation of heteroarenes withChemical science · 2026Article
- Enantioconvergent vinylcyclopropane-cyclopentene rearrangement with vessel-controlled chemodivergence.Nature chemistry · 2026Article
- Synthetic methodologies for the chemical recycling of fluorocarbons.Nature reviews. Chemistry · 2026Review
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Transition-metal catalyzed allylic substitution reactions of alkenes are among the most efficient methods for synthesizing diene compounds, driven by the inherent preference for an inner-sphere mechanism. Here, we present a demonstration of an outer-sphere mechanism in Rh-catalyzed allylic substitution reaction of simple alkenes using gem-difluorinated cyclopropanes as allyl surrogates. This unconventional mechanism offers an opportunity for the fluorine recycling of gem-difluorinated cyclopropanes via C - F bond cleavage/reformation, ultimately delivering allylic carbofluorination products. The developed method tolerates a wide range of simple alkenes, providing access to secondary, tertiary fluorides and gem-difluorides with 100% atom economy. DFT calculations reveal that the C - C bond formation goes through an unusual outer-sphere nucleophilic substitution of the alkenes to the allyl-Rh species instead of migration insertion, and the generated carbon cation then forms the C - F bond with tetrafluoroborate as a fluoride shuttle.
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Registered trials
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