ArticleAngewandte Chemie (International ed. in English)2021
Diastereoselective Synthesis of Aryl C-Glycosides from Glycosyl Esters via C-O Bond Homolysis.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed, 202 citations in OpenAlex.
- Stereodivergent C-(Hetero)Aryl Glycosylation by Nickel-Catalyzed Redox-Neutral Cross-Coupling of Glycosyl Sulfonyl Hydrazides.Angewandte Chemie (International ed. in English) · 2026Article
- Benzodithiolane-Enabled C─O Bond Activation for Deoxygenative Functionalization of Carbohydrates and Nucleosides.Angewandte Chemie (International ed. in English) · 2026Article
- Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.Journal of the American Chemical Society · 2026Article
- eCyclopropanation - a safe and scalable electrochemical route to cyclopropanes.Chemical science · 2026Article
- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- Low-valent cobalt catalyzed direct dehydroxylative cross-coupling of benzyl alcohols with aryl-chlorides.Chemical science · 2026Article
- Direct deoxygenative arylation of saccharides via phosphorus-assisted C-OH bond activation.Nature communications · 2025Article
- Late-Stage Serine Modification Enables Noncanonical Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Synthesis of C4-Acyl Glycosides by Cross-Ketonization: The Importance of Precise Temperature Control in Photochemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Stereoselective Conversions of Carbohydrate Anomeric Hydroxyl Group in Basic and Neutral Conditions.Molecules (Basel, Switzerland) · 2024Review
- Regiodivergent Functionalization of Protected and Unprotected Carbohydrates using Photoactive 4-Tetrafluoropyridinylthio Fragment as an Adaptive Activating Group.Angewandte Chemie (International ed. in English) · 2024Article
- Pd-Catalyzed Stereospecific Glycosyl Cross-Coupling of Reversed Anomeric Stannanes for Modular Synthesis of NonclassicalPrecision chemistry · 2024Article
- Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.Science advances · 2024Article
- Electrochemical Glycosylation via Halogen-Atom-Transfer forACS catalysis · 2024Article
- Diverse Synthesis of C-Glycosides by Stereoselective Ni-Catalyzed Carboboration of Glycals.Journal of the American Chemical Society · 2024Article
- Aromatization-driven deconstructive functionalization of spiro dihydroquinazolinonesChemical science · 2024Article
- Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(spJournal of the American Chemical Society · 2024Article
- Dehydroxylative radical N-glycosylation of heterocycles with 1-hydroxycarbohydrates enabled by copper metallaphotoredox catalysis.Nature communications · 2024Article
- Simplified Modular Access to Enantiopure 1,2-Aminoalcohols via Ni-Electrocatalytic Decarboxylative Arylation.Journal of the American Chemical Society · 2024Article
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
C-aryl glycosyl compounds offer better in vivo stability relative to O- and N-glycoside analogues. C-aryl glycosides are extensively investigated as drug candidates and applied to chemical biology studies. Previously, C-aryl glycosides were derived from lactones, glycals, glycosyl stannanes, and halides, via methods displaying various limitations with respect to the scope, functional-group compatibility, and practicality. Challenges remain in the synthesis of C-aryl nucleosides and 2-deoxysugars from easily accessible carbohydrate precursors. Herein, we report a cross-coupling method to prepare C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from glycosyl esters and bromoarenes. Activation of the carbohydrate substrates leverages dihydropyridine (DHP) as an activating group followed by decarboxylation to generate a glycosyl radical via C-O bond homolysis. This strategy represents a new means to activate alcohols as a cross-coupling partner. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.
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Registered trials
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