ArticleJournal of the American Chemical Society2022
Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
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Who cites it
31 citing papers in PubMed.
- Redox-neutral ketone-olefin coupling enabled by mild ketone-to-ketyl-type radical conversion.Nature chemistry · 2026Article
- Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.Journal of the American Chemical Society · 2026Article
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- Photothermal catalysis versus thermal catalysis: A palladium-catalyzed intermolecular three-component C─H 1,3-Science advances · 2026Article
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- Virtual Ligand-Assisted Screening for the Generation of Ketyl Radicals from Alkyl Ketones via Photoexcited Palladium Catalysis.Journal of the American Chemical Society · 2025Article
- Modular synthesis of PAHs from aryl halides and terminal alkynes via photoinduced palladium catalysis.Nature communications · 2025Article
- Article
- General Modular and Convergent Approach to Diversely Functionalized Allylic Systems.Journal of the American Chemical Society · 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
- Illuminating Palladium Catalysis.Accounts of chemical research · 2025Article
- A New Reaction Framework for Allyl Carboxylates.Trends in chemistry · 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
- Creating glycoside diversity through stereoselective carboboration of glycals.Nature communications · 2024Article
- Radical-triggered translocation of C-C double bond and functional group.Nature chemistry · 2024Article
- Electrochemical Glycosylation via Halogen-Atom-Transfer forACS catalysis · 2024Article
- Article
- Recent Advances in Visible Light Induced Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2024Review
- Transformations of carbohydrate derivatives enabled by photocatalysis and visible light photochemistry.Chemical science · 2024Review
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Authors and funding
7 authors.
Funding
Abstract
Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex molecular architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the preparation of a wide variety of C2-alkenylated carbohydrate mimetics to aid the discovery and development of new therapeutics, agrochemicals, and materials.
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