ArticleNature chemistry2022
Halogen-bond-assisted radical activation of glycosyl donors enables mild and stereoconvergent 1,2-cis-glycosylation.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 148 citations in OpenAlex.
- Enhanced Selectivity of Chalcogen Bonding over Halogen Bonding Catalyzed C-glycosylation Through Differentiated Intermediate Activation.Angewandte Chemie (International ed. in English) · 2026Article
- Dual Semiconductor-Photoredox/Halogen-Bonding Organocatalyzed Cascade Sulfonylation/Cyclization of Alkynes and Alkenes with RSOAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Sustainable Natural Product Glycosylation: A Critical Evaluation of Biocatalytic and Chemical Approaches.ChemSusChem · 2025Review
- Catalytic Strategies for Stereoselective Carbohydrate Synthesis: Emerging Concepts for Accessing Challenging Glycosides.Angewandte Chemie (International ed. in English) · 2025Review
- Emerging Capabilities of Nonclassical Noncovalent Interactions and Asymmetric Catalysis in Stereoselective Glycosylations and Carbohydrate Functionalizations.Accounts of chemical research · 2025Article
- Isothiourea - catalyzed α-selective glycosylations.Chemical communications (Cambridge, England) · 2025Article
- Defluorinative Cyclization of Enamides with Fluoroalkyl Halides Through Two Vicinal C(spAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Regiodivergent Functionalization of Protected and Unprotected Carbohydrates using Photoactive 4-Tetrafluoropyridinylthio Fragment as an Adaptive Activating Group.Angewandte Chemie (International ed. in English) · 2024Article
- Catalyst-free and wavelength-tuned glycosylation based on excited-state intramolecular proton transfer.Nature communications · 2024Article
- Article
- Direct radical functionalization of native sugars.Nature · 2024Article
- Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes.Nature communications · 2024Article
- Dehydroxylative radical N-glycosylation of heterocycles with 1-hydroxycarbohydrates enabled by copper metallaphotoredox catalysis.Nature communications · 2024Article
- Harnessing Multistep Chalcogen Bonding Activation in the α-Stereoselective Synthesis of Iminoglycosides.Journal of the American Chemical Society · 2024Article
- EfficientChemical science · 2024Article
- Chemoenzymatic indican for light-driven denim dyeing.Nature communications · 2024Article
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
- Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.Journal of the American Chemical Society · 2023Article
- Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors.Nature communications · 2023Article
- Photochemical halogen-bonding assisted carbothiophosphorylation reactions of alkenyl and 1,3-dienyl bromides.Chemical science · 2023Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The chemistry of carbohydrates has a history of over 100 years, but simple, stereoselective and efficient glycosylation methods remain highly needed to facilitate the studies of sugars in various disciplines. Here we report a strategy for 1,2-cis-glycosylation without using metals, strong (Lewis) acids, elaborate catalysts or labile substrates. Our method operates by a unique mechanism: it activates glycosyl donors through a radical cascade rather than the conventional acid-promoted, ionic process. As elucidated by computational and experimental studies, the allyl glycosyl sulfones (as donors) form halogen bond complexes with perfluoroalkyl iodides, which-merely by visible light irradiation-fragment via radical intermediates to give the electrophilic glycosyl iodides. In situ trapping by various nucleophiles affords, in a stereoconvergent manner, the challenging 1,2-cis-glycosides. This metal- and acid-free reaction shows remarkable tolerance to functional groups. The high stereoselectivity holds for a broad array of donors. This study suggests that the simple C2-alkoxy group can serve as an effective directing group for building 1,2-cis-glycosidic bonds.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.