ArticleJournal of the American Chemical Society2021
Nickel-Catalyzed Radical Migratory Coupling Enables C-2 Arylation of Carbohydrates.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.Journal of the American Chemical Society · 2026Article
- Article
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Article
- Asymmetric synthesis of β-amino acid derivatives by stereocontrolled C(spNature communications · 2025Article
- Photoinduced Ruthenium-CatalyzedACS catalysis · 2025Article
- Catalytic 1,2-Radical Acyloxy Migration: A Strategy to Access Novel Chemical Space and Reaction Profiles.Accounts of chemical research · 2025Article
- Excited-State Palladium-Catalyzed Radical Allylic Alkylation: Rapid Access to C2-Allyl Carbohydrates.ACS catalysis · 2025Article
- A New Reaction Framework for Allyl Carboxylates.Trends in chemistry · 2025Article
- Stereoselective and site-divergent synthesis of C-glycosides.Nature chemistry · 2024Article
- Creating glycoside diversity through stereoselective carboboration of glycals.Nature communications · 2024Article
- Electrochemical Glycosylation via Halogen-Atom-Transfer forACS catalysis · 2024Article
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
- Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock.The Journal of organic chemistry · 2023Article
- 1,2-Radical Shifts in Photoinduced Synthetic Organic Transformations: A Guide to the Reactivity of Useful Radical Synthons.ACS organic & inorganic Au · 2022Review
- Excited-State Copper-Catalyzed [4 + 1] Annulation Reaction Enables Modular Synthesis of α,β-Unsaturated-γ-Lactams.Journal of the American Chemical Society · 2022Article
- Exploiting photoredox catalysis for carbohydrate modification through C-H and C-C bond activation.Nature reviews. Chemistry · 2022Review
- Remote C-H Glycosylation by Ruthenium(II) Catalysis: Modular Assembly of meta-C-Aryl Glycosides.Angewandte Chemie (International ed. in English) · 2022Article
- Selective Axial-to-Equatorial Epimerization of Carbohydrates.Journal of the American Chemical Society · 2022Article
- C2-ketonylation of carbohydratesChemical science · 2022Article
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Authors and funding
6 authors.
Funding
Abstract
Nickel catalysis offers exciting opportunities to address unmet challenges in organic synthesis. Herein we report the first nickel-catalyzed radical migratory cross-coupling reaction for the direct preparation of 2-aryl-2-deoxyglycosides from readily available 1-bromosugars and arylboronic acids. The reaction features a broad substrate scope and tolerates a wide range of functional groups and complex molecular architectures. Preliminary experimental and computational studies suggest a concerted 1,2-acyloxy rearrangement via a cyclic five-membered-ring transition state followed by nickel-catalyzed carbon-carbon bond formation. The novel reactivity provides an efficient route to valuable C-2-arylated carbohydrate mimics and building blocks, allows for new strategic bond disconnections, and expands the reactivity profile of nickel catalysis.
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Registered trials
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