ArticleOrganic letters2015
Copper-Catalyzed Cyclopropanol Ring Opening Csp(3)-Csp(3) Cross-Couplings with (Fluoro)Alkyl Halides.
Article in Organic letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Divergent Synthesis of β-Fluoroamides via Silver-Catalyzed Oxidative Deconstruction of Cyclopropanone Hemiaminals.Organic letters · 2023Article
- Palladium-catalyzed selective C-C bond cleavage and stereoselective alkenylation between cyclopropanol and 1,3-diyne: one-step synthesis of diverse conjugated enynes.Chemical science · 2022Article
- Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides.Molecules (Basel, Switzerland) · 2021Article
- Cu-catalyzed hydroxycyclopropanol ring-opening cyclization to tetrahydrofurans and tetrahydropyrans: short total syntheses of hyperiones.Chemical science · 2020Article
- Nickel-catalyzed reductive coupling of homoenolates and their higher homologues with unactivated alkyl bromides.Nature communications · 2020Article
- Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C-C Bonds.Molecules (Basel, Switzerland) · 2019Review
- Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis.Chemical science · 2018Article
- Catalytic Cyclopropanol Ring Opening for Divergent Syntheses of γ-Butyrolactones and δ-Ketoesters Containing All-Carbon Quaternary Centers.ACS catalysis · 2018Article
- Radical Cyclopropanol Ring Opening Initiated Tandem Cyclizations for Efficient Synthesis of Phenanthridines and Oxindoles.Synlett : accounts and rapid communications in synthetic organic chemistry · 2017Article
- Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols.Journal of the American Chemical Society · 2016Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Novel and general copper-catalyzed cyclopropanol ring opening cross-coupling reactions with difluoroalkyl bromides, perfluoroalkyl iodides, monofluoroalkyl bromides, and 2-bromo-2-alkylesters to synthesize various β-(fluoro)alkylated ketones are reported. The reactions feature mild conditions and excellent functional group compatibility and can be scaled up to gram scale. Preliminary mechanistic studies suggest the involvement of radical intermediates. The difluoroalkyl-alkyl cross-coupling products can also be readily converted to more valuable and diverse gem-difluoro-containing compounds by taking advantage of the carbonyl group resulting from cyclopropanol ring opening.
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